1
Supporting Information
Enantioselective total Syntheses and determination of absolute
configuration of marine toxins, oxazinins.
Dattatraya H. Dethe* and Alok Ranjan
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur – 208016, India
Tel: + 91-512-2596537, Fax: + 91-512-2597436.
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Table of Contents:
NMR of Compound 15, 17, 18: ........................................................................................3
NMR of Compound 19, 20, 22: ........................................................................................7
NMR of Compound 24, 26, 27: ......................................................................................12
NMR of Compound 21, 23, 25: ......................................................................................22
NMR of Compound 13, 28: ............................................................................................27
NMR of Compound 30: ..................................................................................................33
NMR of Compound 34: ..................................................................................................47
NMR of Compound 35 : .................................................................................................48
NMR of compound 10: ...................................................................................................21
NMR of Compound 11: ..................................................................................................18
NMR of Compound 7: ....................................................................................................35
NMR of Compound 9: ....................................................................................................31
NMR of Compound 5: ....................................................................................................40
NMR of Compound 6 :....................................................................................................44
NMR of Compound 1: ....................................................................................................50
NMR of Compound 2: ....................................................................................................53
NMR of Compound 4: ....................................................................................................51
CD Spectra of Oxazinin-5: .............................................................................................55
CD Spectra of Preoxazinin-7: ........................................................................................56
CD Spectra of Oxazinin-6: .............................................................................................57
HPLC of Compound 21: .............................................................................................59
NMR Spectrum:
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30 May 2011Alok
Z:\AV200\OCT_09~1\data\ADMINI~1\nmr\MOE13D~1\1\pdata\1\1r
Acquisition Time (sec) 7.9167 Comment Alok Date 19/10/2009 15:38:24 Frequency (MHz) 200.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 4139.07
Temperature (grad C) 0.000
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0
6.89 3.062.02 2.00 1.960.97 0.96
Chloroform-d
1.30
1.33
1.37
4.20
4.24
4.27
4.31
5.10
6.27
6.35
6.95
7.00
7.26
7.36
7.37
7.40
7.41
7.42
7.45
7.49
7.50
7.60
7.68
30 May 2011Alok
Z:\AV200\OCT_09~1\data\ADMINI~1\nmr\WEFC94~1\1\pdata\1\1r
Acquisition Time (sec) 2.7329 Comment Alok Date 22/10/2009 07:47:24 Frequency (MHz) 50.32
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
Chloroform-d14
.33
60.3
2
70.0
6
76.3
677
.00
77.6
3
115.
1811
5.87
127.
4412
8.13
128.
6412
9.68
136.
45
144.
17
160.
47
167.
31
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Sat2av2#029.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
3.000.850.913.011.012.052.066.95
0.00
1.22
1.25
1.29
1.65
2.73
2.76
3.15
3.18
4.19
4.23
4.26
4.29
4.30
4.31
4.33
4.91
4.93
4.94
4.96
5.06
6.95
6.99
7.25
7.31
7.34
7.35
7.37
7.38
7.41
7.44
30 May 2011Alok
Z:\AV200\OCT_09~1\data\ADMINI~1\nmr\WEFC94~1\2\pdata\1\1r
Acquisition Time (sec) 2.7329 Comment Alok Date 22/10/2009 08:22:32 Frequency (MHz) 50.32
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
14.3
9
60.3
8
70.0
9
115.
2111
5.90
127.
5012
8.19
128.
7012
9.74
144.
23
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Wed3av2#064.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
14.0
6
62.1
1
69.9
6
74.1
874
.69
76.3
777
.00
77.6
4
114.
73
127.
4112
7.61
127.
9412
8.55
132.
31
136.
85
158.
56
172.
74
Wed3av2#064.002.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
14.1
3
62.1
9
70.0
374
.25
74.7
6
114.
80
127.
4812
7.68
128.
0312
8.64
OBn
CO2Et
OHHO
(CDCl3, 25 °C)17
OBn
CO2Et
OHHO
(CDCl3, 25 °C)17
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Wed3av2#027.001.001.1r.esp
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.101.092.001.041.820.951.961.984.821.941.91
1.14
1.17
1.21
2.59
4.10
4.14
4.17
4.21
4.94
4.96
4.99
5.13
5.15
6.78
6.82
7.11
7.15
7.26
7.36
7.37
7.39
7.40
7.41
7.42
7.43
7.81
7.86
7.87
8.19
8.23
8.24
Sat3av2#058.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
13.8
4
62.4
7
69.9
273
.04
76.3
677
.00
77.6
3
82.4
2
114.
69
124.
0412
7.41
127.
5312
8.10
128.
5912
9.09
129.
5213
6.39
141.
37
150.
45
158.
93
166.
42
(CDCl3, 25 °C)18
OBn
CO2Et
ONsHO
(CDCl3, 25 °C)18
OBn
CO2Et
ONsHO
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Sat3av2#058.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
13.9
4
62.5
8
70.0
1
73.1
4
82.5
2
114.
78
124.
1412
7.51
127.
6312
8.21
128.
6912
9.19
Sat4av2#004.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
3.041.280.870.911.950.981.981.977.62
0.00
1.24
1.28
1.31
1.58
2.77
2.80
4.07
4.11
4.20
4.24
4.27
4.31
4.95
4.97
4.98
5.01
5.07
6.96
6.97
7.00
7.01
7.26
7.30
7.34
7.35
7.36
7.39
7.42
(CDCl3, 25 °C)18
OBn
CO2Et
ONsHO
OBn
CO2Et
N3HO
19CDCl3, 25 °C
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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Wed3av2#063.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
14.0
4
62.1
3
66.7
8
69.9
873
.66
76.3
777
.00
77.6
4
114.
90
127.
4312
7.93
127.
9912
8.58
131.
28
136.
72
159.
04
168.
95
Wed3av2#063.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
14.1
3
62.2
0
66.8
4
70.0
4
73.7
4
114.
97
127.
5112
8.01
128.
65
OBn
CO2Et
N3HO
19CDCl3, 25 °C
OBn
CO2Et
N3HO
19CDCl3, 25 °C
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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Mon4av2#009.001.001.1r.esp
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
3.008.782.750.822.060.880.831.991.904.82
1.15
1.19
1.22
1.43
4.04
4.08
4.11
4.15
4.18
4.61
4.63
4.65
4.67
5.04
5.12
5.30
5.34
6.90
6.94
6.95
7.17
7.21
7.33
7.35
7.37
7.37
7.39
7.40
7.41
OBn
CO2Et
NHBocHO
20(CDCl3, 25 °C)
OXABOC_13C-2.jdf
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
13.9
7
28.1
9
59.6
761
.62
69.9
174
.60
76.6
777
.00
77.3
280
.50
114.
52
127.
2912
7.38
127.
9012
8.51
131.
57
136.
84
156.
3315
8.48
169.
85
CO2Et
NHBocHO
OBn
(CDCl3, 25 °C)20
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OXABOX_DEPT-2.jdf
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
128.
6712
8.06
127.
5412
7.44
114.
67
74.7
6
70.0
7
61.7
859
.82
28.3
4
14.1
3
CO2Et
NHBocHO
OBn(CDCl3, 25 °C)
20
Thu3av2#009.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.004.1610.983.159.402.060.873.030.812.197.58
-0.1
9
0.00
0.01
0.84
1.01
1.05
1.08
1.34
3.93
3.96
4.00
4.03
4.38
4.40
4.43
4.45
4.94
5.20
5.24
6.83
6.87
7.18
7.21
7.22
7.24
7.25
7.28
7.31
7.34
7.35
OBn
CO2Et
NHBocTBSO
(CDCl3, 25 °C)
22
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Sat3av2#059.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.5
3-5
.02
13.7
9
17.8
8
25.5
028
.09
60.6
060
.77
69.6
774
.94
76.3
777
.00
77.6
479
.34
114.
03
127.
2312
7.68
128.
3013
2.70
136.
78
154.
61
158.
07
169.
70
OBn
CO2Et
NHBocTBSO
(CDCl3, 25 °C)22
Sat3av2#059.001.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.2
6-4
.75
14.0
6
25.7
728
.36
60.8
7
61.04
69.93
75.2
1
114.
29
127.
5112
8.57
OBn
CO2Et
NHBocTBSO
(CDCl3, 25 °C)22
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Thu3av2#008.001.001.1r.esp
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.023.009.132.799.021.980.770.890.762.032.020.95
-0.1
9
0.00
0.84
1.08
1.12
1.15
1.37
3.99
4.03
4.06
4.10
4.41
4.43
4.45
4.47
4.92
4.94
5.25
5.29
6.71
6.75
7.09
7.14
7.25
7.49
OH
CO2Et
NHBocTBSO
(CDCl3, 25 °C)24
Sat3av2#057.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.5
0-4
.94
13.8
3
17.9
3
25.5
328
.17
60.7
361
.21
75.0
776
.36
77.0
077
.64
80.1
0
114.
91
127.
38
131.
34
155.
1515
5.99
170.
37
OH
CO2Et
NHBocTBSO
(CDCl3, 25 °C)24
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Sat3av2#057.001.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.3
7-4
.81
13.9
7
25.6
728
.07
28.3
1
60.8
561
.35
75.1
9
115.
04
127.
51
OH
CO2Et
NHBocTBSO
(CDCl3, 25 °C)24
Fri3av2#014.001.001.1r.esp
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.032.979.123.069.012.001.942.090.860.880.832.042.11
-0.1
9
0.00
0.84
1.07
1.10
1.14
1.36
2.74
2.77
2.80
3.97
4.01
4.04
4.08
4.10
4.13
4.16
4.41
4.94
4.96
5.18
5.22
6.78
6.83
7.21
7.23
7.25
O
CO2Et
NHBocTBSO
CN
(CDCl3, 25 °C)26
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Sat3av2#079.002.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.4
4-4
.96
13.9
317
.97
18.4
9
25.5
528
.18
60.7
260
.98
62.4
9
74.9
876
.37
77.0
077
.64
79.6
1
113.
95
117.
13
127.
49
133.
86
154.
7115
7.04
169.
65
O
CO2Et
NHBocTBSO
CN(CDCl3, 25 °C)
26
Sat3av2#079.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.4
1-4
.93
13.9
6
18.5
3
25.5
8
28.2
1
60.7
561
.01
62.5
1
75.0
0
113.
97
127.
52
O
CO2Et
NHBocTBSO
CN(CDCl3, 25 °C)
26
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Sat3av2#011.001.001.1r.esp
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
3.003.139.719.232.272.141.082.140.920.822.142.42
-0.1
8
0.00
0.84
1.38
2.73
2.76
2.79
3.34
3.40
3.45
3.48
3.72
3.74
3.78
3.79
4.09
4.12
4.15
5.06
5.37
5.41
6.79
6.83
7.23
7.27
O
CH2OH
NHBocTBSO
CN(CDCl3, 25 °C)
26a
Tue3av2#073.002.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.4
8-5
.05
17.9
618
.52
25.7
028
.31
56.5
6
60.9
762
.52
76.3
676
.85
77.0
077
.63
79.4
1
114.
3111
7.10
127.
13
134.
34
155.
5515
6.93
O
CH2OH
NHBocTBSO
CN
26a
(CDCl3, 25 °C)
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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Tue3av2#073.001.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.5
0-5
.07
18.5
1
25.6
8
28.2
9
56.5
2
60.9
462
.49
76.8
3
114.
28
127.
10
O
CH2OH
NHBocTBSO
CN
26a(CDCl3, 25 °C)
Thu1av2#001.001.001.1r.esp
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
2.813.019.002.270.851.572.400.750.662.342.530.83
-0.1
5
0.05
0.90
2.80
2.83
2.86
3.40
3.42
3.46
3.48
3.86
3.87
3.93
3.96
3.98
4.15
4.18
4.21
5.09
5.11
6.49
6.53
6.86
6.91
7.25
7.29
7.33
8.25
CH2OH
NHCHOTBSO
O CN(CDCl3, 25 °C)
27a
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
17
Sun3av2#022 c13 tbs bursatelline.002.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
-5.2
8-4
.88
17.9
818
.62
25.7
7
54.5
7
60.7
662
.60
76.3
776
.64
77.0
077
.63
114.
5211
7.09
127.
3112
8.02
133.
99
157.
24
161.
00
CH2OH
NHCHOTBSO
O CNCDCl3, 25 °C
27a
Sun3av2#022 c13 tbs bursatelline.001.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
-5.2
2-4
.82
18.6
9
25.8
3
54.5
9
60.8
262
.64
76.7
3
114.
57
127.
36
161.
07
CH2OH
NHCHOTBSO
O CNCDCl3, 25 °C
27a
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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Fri4av400#004.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0.962.000.881.401.241.021.981.000.971.931.800.91
2.57
2.83
2.85
2.87
3.06
3.65
3.68
3.88
3.88
3.91
3.91
4.13
4.14
4.15
4.16
4.20
4.22
4.23
5.06
5.06
6.42
6.43
6.93
6.95
7.27
7.36
7.38
8.27
O
CH2OH
NHCHOHO
CN(CDCl3, 25 °C)
epi-bursatellin (11)
Fri4av400#004.003.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
18.6
6
29.7
1
54.2
3
61.4
062
.74
75.4
376
.69
77.0
177
.22
77.3
3
114.
8511
7.07
127.
21
133.
92
157.
48
161.
28
O
CH2OH
NHCHOHO
CN(CDCl3, 25 °C)
epi-bursatellin (11)
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
19
Fri4av400#004.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
18.6
6
54.2
4
61.4
062
.74
75.4
377
.21
90.3
0
114.
85
127.
21
161.
28
O
CH2OH
NHCHOHO
CN
epi-bursatellin (11)
(CDCl3, 25 °C)
Mon4av2#010.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.002.959.151.162.000.881.032.042.010.972.014.950.901.000.990.91
-0.1
50.
000.
07
0.92
1.75
2.79
2.82
2.85
3.03
3.06
3.60
3.64
3.68
3.71
3.94
3.95
4.00
4.03
4.05
4.13
4.16
4.19
5.04
5.06
6.84
6.89
7.26
7.29
7.30
7.32
7.34
7.35
7.36
7.41
7.42
8.10
8.15
8.41
8.43
8.44
8.45
8.87
8.89
9.27
NH
O
HN
O
OCN
OTBS
OH(CDCl3, 25 °C)
27b
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
20
Mon4av2#057.002.001.1r.esp
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.2
9-4
.88
17.9
918
.66
25.7
5
56.2
3
61.0
562
.49
75.8
076
.37
77.0
077
.63
111.
6811
3.20
114.
3811
7.40
122.
4012
3.32
124.
1612
6.53
127.
52
134.
1813
5.72
138.
05
157.
17
162.
47
180.
36
NH
O
HN
O
OCN
OTBS
OH
(CDCl3, 25 °C)27b
Mon4av2#057.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.2
3-4
.82
18.7
2
25.8
1
56.2
8
61.1
162
.54
75.8
7
111.
74
114.
44
122.
4612
3.39
124.
2212
7.58
138.
13
NH
O
HN
O
OCN
OTBS
OH
(CDCl3, 25 °C)27b
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
21
Thu4av2#008.001.001.1r.esp
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
1.812.000.891.970.932.960.982.014.110.970.860.990.980.58
0.00
2.78
2.81
2.84
3.20
3.23
3.26
3.60
3.66
3.68
3.73
3.76
3.79
3.91
3.93
4.09
4.12
4.15
4.17
4.80
4.82
4.83
4.85
6.85
6.88
6.89
7.25
7.27
7.28
7.29
7.30
7.32
7.32
7.36
7.51
7.54
7.69
8.25
8.26
8.29
8.77
8.78
10.1
9
NH
O
HN
O
OCN
OH
OH
Synthetic epi-Preoxazinin-7 (10)(200 MHz, CD3CN, 25 °C)
ALOK.ESP
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
0.85
1.26
1.67
2.09
2.50
2.91
19.4
6
57.4
9
62.2
064
.25
74.2
5
113.
6211
3.72
115.
4711
8.69
119.
6012
2.98
124.
2212
5.12
127.
8312
9.26
136.
2913
7.49
140.
11
158.
73
163.
72
182.
38
NH
O
HN
O
OCN
OH
OH
Synthetic epi-Preoxazinin-7 (10)(50 MHz, CD3CN, 25 °C)
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
22
ALOKDEPT.ESP
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
19.4
6
57.4
8
62.1
964
.23
74.2
2
113.
6211
5.45
122.
9812
4.23
125.
1212
9.25
140.
13
NH
O
HN
O
OCN
OH
OH
Synthetic epi-Preoxazinin-7 (10)(50 MHz, CD3CN, 25 °C)
22 Dec 2010
Acquisition Time (sec) 7.9167 Comment Alok/10997 Date 28/04/2010 11:04:28
Frequency (MHz) 200.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 4139.07
Temperature (grad C) 0.000
1 0 . 0 9 . 5 9 . 0 8 . 5 8 . 0 7 . 5 7 . 0 6 . 5 6 . 0 5 . 5 5 . 0 4 . 5 4 . 0 3 . 5 3 . 0 2 . 5 2 . 0 1 . 5 1 . 0 0 . 5 0 . 0
1 1 . 9 77 . 0 2 2 . 9 92 . 0 0 2 . 0 0 0 . 9 30 . 9 10 . 8 6
0.00
1.19
1.22
1.35
2.91
4.12
4.16
4.19
4.23
4.47
5.04
5.12
5.33
6.92
6.96
6.97
7.24
7.26
7.38
7.40
7.43
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
23
22 Dec 2010
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 01/05/2010 23:30:30
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
2 0 0 1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0
14.1
2
28.2
4
59.6
661
.67
70.0
1
73.7
376
.47
77.1
177
.74
80.0
9
114.
71
127.
4112
7.46
128.
62
132.
37136.
94
158.
59
171.
02
22 Dec 2010
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 01/05/2010 23:11:08
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0
14.1
3
28.2
4
61.6870.01
73.7
2
114.
70
127.
4712
8.63
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
24
22 Dec 2010
Acquisition Time (sec) 7.9167 Comment Alok/10997 Date 01/07/2010 15:37:50
Frequency (MHz) 200.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 4139.07
Temperature (grad C) 0.000
1 0 . 0 9 . 5 9 . 0 8 . 5 8 . 0 7 . 5 7 . 0 6 . 5 6 . 0 5 . 5 5 . 0 4 . 5 4 . 0 3 . 5 3 . 0 2 . 5 2 . 0 1 . 5 1 . 0 0 . 5 0 . 0 - 0 . 5 - 1 . 0
1 2 . 0 58 . 9 57 . 0 2 3 . 6 0 3 . 1 13 . 0 12 . 0 0
-0.1
50.
00
0.89
1.18
1.27
1.31
1.35
4.21
4.35
4.41
5.05
5.24
6.91
6.96
7.25
7.29
7.36
7.37
7.40
7.40
7.42
7.44
22 Dec 2010
Acquisition Time (sec) 2.7329 Comment Alok Ranjan Date 18/04/2010 05:15:18
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
2 0 0 1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0 - 1 0 - 2 0
-5.2
6-4
.75
14.0
6
18.1
5
25.7
728
.35
61.0
4
69.9
4
75.2
1
79.6
1
114.
30
127.
5012
8.57
132.
97
137.
05
154.
8815
8.34
169.
97
CO2Et
NHBocTBSO
OBn
23
(CDCl3, 25 °C)
CO2Et
NHBocTBSO
OBn
23
(CDCl3, 25 °C)
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
25
22 Dec 2010
Acquisition Time (sec) 2.7329 Comment Alok Ranjan Date 18/04/2010 04:55:30
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0 - 1 0
-5.2
6-4
.75
14.0
6
25.7
728
.35
60.8
761
.04
69.9
3
75.2
1
114.
29
127.
5112
7.96
128.
57
28 May 2011Alok/10997 ( 303K)
Z:\AV400\JAN_11~1\SUN4AV~1\2\pdata\1\1r
Acquisition Time (sec) 3.9846 Comment Alok/10997 ( 303K) Date 16/01/2011 16:21:56
Frequency (MHz) 400.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8223.68
Temperature (grad C) 0.000
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
12.58 9.313.07 3.032.011.97 1.050.84
-0.1
5
0.01
0.89
1.27
1.36
4.14
4.17
4.19
4.21
4.24
5.22
5.49
5.51
6.77
6.79
6.97
7.21
7.23
CO2Et
NHBocTBSO
OBn
23
(CDCl3, 25 °C)
CO2Et
NHBocTBSO
OH
25
CDCl3, 25 °C
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
26
22 Dec 2010
Acquisition Time (sec) 1.3631 Date 22/12/2010 20:26:28 Frequency (MHz) 100.61 Nucleus 13C
Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46 Temperature (grad C) 0.000
2 0 0 1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0 - 1 0
-5.5
5-4
.59
14.1
1
18.0
7
25.6
828
.29
60.8
361
.63
74.5
576
.74
77.0
677
.38
80.2
3
115.
04
127.
42
131.
84
155.
8815
6.07
170.
87
22 Dec 2010
Acquisition Time (sec) 1.3631 Date 09/07/2010 18:45:58 Frequency (MHz) 100.61 Nucleus 13C
Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46 Temperature (grad C) 0.000
2 0 0 1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0
14.1
1
25.6
828
.29
60.8
361
.63
62.1
6
74.5
5
115.
04
127.
42
CO2Et
NHBocTBSO
OH
25
CDCl3, 25 °C
CO2Et
NHBocTBSO
OH
25
CDCl3, 25 °C
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
27
2 May 2011Alok/10997
Acquisition Time (sec) 7.9167 Comment Alok/10997 Date 28/04/2011 10:47:56
Frequency (MHz) 200.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 4139.07
Temperature (grad C) 0.000
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5 -1.0
12.09 8.985.05 2.992.06 2.00 1.981.92
-0.1
50.
00
0.89
1.19
1.28
1.32
1.35
2.79
2.82
2.85
4.15
4.18
4.21
4.25
4.34
4.35
4.39
4.40
5.20
5.25
5.30
6.85
6.89
7.27
7.31
9 May 2011Alok/10997
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 07/05/2011 03:00:28
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
Chloroform-d
-5.6
9-4
.77
13.9
817
.89
18.4
1
25.5
028
.08
60.4
661
.32
62.4
7
74.2
276
.37
77.0
077
.64
79.4
6
114.
0611
7.09
127.
48
133.
94
155.
2615
7.08
170.
46
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
28
9 May 2011Alok/10997
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 07/05/2011 02:21:42
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-5.5
2-4
.60
14.1
5
18.5
7
25.6
628
.24
60.6
361
.49
62.6
3
74.3
8
114.
21
127.
64
20 Jan 2011
Acquisition Time (sec) 7.9167 Comment Alok/10997 Date 28/04/2010 15:37:50
Frequency (MHz) 200.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 4139.07
Temperature (grad C) 0.000
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5 -1.0
9.229.043.10 3.002.272.12 2.062.02 1.56
TMS
-0.1
6
0.05
0.88
0.90
1.37
2.79
2.82
2.86
3.62
4.14
4.18
4.21
4.88
4.89
6.83
6.84
6.87
7.22
7.27
CH2OH
NHBocTBSO
O CNCDCl3, 25 °C
28
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
29
30 May 2011Alok/10997
Z:\AV200\MAY_10~1\data\ADMINI~1\nmr\SA0B7F~1\2\pdata\1\1r
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 02/05/2010 13:24:16
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
Chloroform-d
-5.3
2-4
.70
18.0
218
.51
25.7
228
.21
58.4
9
62.5
162
.73
72.9
276
.37
77.0
077
.64
79.4
8
114.
1911
7.16
127.
56
135.
02
156.
0615
6.97
30 May 2011Alok/10997
Z:\AV200\MAY_10~1\data\ADMINI~1\nmr\SA0B7F~1\1\pdata\1\1r
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 02/05/2010 13:04:54
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-5.2
0-4
.59
18.6
3
25.8
428
.33
58.6
0
62.6
262
.86
73.0
3
114.
30
127.
68
CH2OH
NHBocTBSO
O CNCDCl3, 25 °C
28
CH2OH
NHBocTBSO
O CNCDCl3, 25 °C
28
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
30
20 May 20111H
Acquisition Time (sec) 3.2768 Comment 1H Date 25/05/2010 22:14:54 Frequency (MHz) 500.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 10000.00
Temperature (grad C) 0.000
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0
9.51 3.012.942.51 2.182.03 2.00 1.861.000.970.94
TMS
-0.1
40.
000.
08
0.91
2.82
2.83
2.84
3.67
3.69
4.03
4.04
4.05
4.17
4.19
4.20
4.80
4.81
4.97
6.07
6.08
6.85
6.87
7.24
7.27
8.14
TBS-Protected Bursatellin20 May 201113C
Acquisition Time (sec) 1.1010 Comment 13C Date 26/05/2010 13:13:32 Frequency (MHz) 125.76
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 29761.90
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-5.2
2-4
.58
18.1
518
.65
25.8
3
57.1
960
.78
62.6
262
.97
72.2
773
.46
114.
4811
7.17
127.
3912
7.79
134.
68
157.
25
161.
59
164.
99
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
31
TBS-Protected Bursatellin20 May 2011Alok/10997
Acquisition Time (sec) 2.7329 Comment Alok/10997 Date 06/11/2010 16:10:58
Frequency (MHz) 50.32 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 11990.41
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-5.2
0-4
.59
18.6
5
25.7
8
62.1
862
.58
71.9
473
.41
114.
38
127.
3912
7.85
161.
89
(-)-Bursatellin19 May 2011Thu2av400#009Alok
Acquisition Time (sec) 3.9846 Comment Alok Date 07/02/2011 09:30:44 Frequency (MHz) 400.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8223.68
Temperature (grad C) 0.000
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0
2.08 2.022.01 1.99 1.901.210.76
methenol
2.78
2.79
2.81
3.19
3.35
3.36
3.39
3.52
3.54
3.56
3.98
3.99
4.05
4.06
4.08
4.78
4.79
6.80
6.82
7.21
7.23
7.89
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
32
(-)-Bursatellin19 May 2011Thu2av400#009Alok
Acquisition Time (sec) 1.2976 Comment Alok Date 07/02/2011 09:31:46 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 25252.53
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
19.0
0
57.1
3
62.5
264
.19
71.9
2
115.
34
119.
17
128.
64
136.
73
158.
87
164.
00
(-)-Bursatellin19 May 2011Thu2av400#009Alok
Acquisition Time (sec) 1.2976 Comment Alok Date 07/02/2011 09:30:54 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 25252.53
Temperature (grad C) 0.000
220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 -20
16.0
4
54.1
7
59.5
661
.22
68.9
5
112.
37
125.
68
161.
04
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
33
3 Jan 2011
Acquisition Time (sec) 3.9846 Comment Alok/10997 Date 03/01/2011 16:27:34
Frequency (MHz) 400.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8223.68
Temperature (grad C) 0.000
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
9.385.50 3.12 3.002.102.10 2.061.02 1.001.00 0.990.97
TMS
-0.1
50.
000.
07
0.92
2.71
2.73
2.74
3.74
3.79
4.02
5.00
6.72
6.74
7.21
7.24
7.26
7.29
7.31
7.34
7.36
7.91
7.93
8.38
8.40
8.70
8.71
8.72
9.58
3 Jan 2011
Acquisition Time (sec) 1.3631 Comment 13C Date 03/01/2011 16:27:50 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
Chloroform-d
-5.2
5-4
.61
18.1
018
.55
25.7
8
58.1
1
62.3
662
.73
72.7
376
.69
77.0
077
.32
111.
8511
2.94
114.
2711
7.43
122.
2112
3.27
124.
0612
6.51
127.
44
134.
7413
5.80
138.
50
157.
06
163.
00
180.
25
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
34
3 Jan 2011
Acquisition Time (sec) 1.3631 Comment DEPT Date 03/01/2011 16:27:42 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
18.6
0
25.8
3
58.1
6
62.4
162
.78
72.7
8
111.
8911
4.31
122.
2612
3.32
124.
1112
7.49
138.
56
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
35
Preoxazinin18 May 2011Thu2av400#009Alok R/10997
Acquisition Time (sec) 3.9846 Comment Alok R/10997 Date 17/05/2010 21:04:00
Frequency (MHz) 400.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8223.68
Temperature (grad C) 0.000
11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
4.13 2.03 2.001.96 1.181.03 1.010.950.93 0.910.77
TMSAcetonitrile-d3
-0.0
1
2.16
2.78
2.80
2.81
3.16
3.18
3.59
3.62
3.64
3.68
3.70
3.84
4.04
4.06
4.11
4.13
4.14
4.98
4.98
6.86
6.88
7.29
7.30
7.32
7.52
7.53
7.54
7.55
7.77
7.80
8.31
8.81
10.1
2
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
36
23 Dec 2010
Acquisition Time (sec) 1.3631 Comment Alok R/10997 Date 18/05/2010 10:30:42
Frequency (MHz) 100.61 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
2 0 0 1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0 0
A c e t o n it r ile - d 3
19.1
9
57.7
8
63.1
264
.00
72.5
0
113.
3311
5.25
118.
3812
2.74
123.
9712
4.86
128.
47
136.
5013
7.21
139.
88
158.
38
163.
59
181.
99
23 Dec 2010
Acquisition Time (sec) 1.3631 Comment Alok R/10997 Date 18/05/2010 18:39:38
Frequency (MHz) 100.61 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
1 9 0 1 8 0 1 7 0 1 6 0 1 5 0 1 4 0 1 3 0 1 2 0 1 1 0 1 0 0 9 0 8 0 7 0 6 0 5 0 4 0 3 0 2 0 1 0
18.1
3
56.7
2
62.0
662
.94
71.4
3
112.
2711
4.19
121.
6812
2.90
123.
7912
7.41
138.
81NH
O
HN
O
OCN
OH
OH
Synthetic Preoxazinin-7 (7)(100 MHz, CD3CN, 25 °C)
NH
O
HN
O
OCN
OH
OH
Synthetic Preoxazinin-7 (7)(100 MHz, CD3CN, 25 °C)
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
37
TBS-protected oxazinin-528 Apr 2011mon5av400#002VHP
Acquisition Time (sec) 3.9846 Comment Alok Date 28/03/2011 15:45:38 Frequency (MHz) 400.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8223.68
Temperature (grad C) 0.000
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
9.494.00 3.103.032.19 2.112.112.09 1.071.051.03 1.031.001.00
TMS
-0.1
9
0.00
0.10
0.91
2.81
2.83
2.84
3.39
3.40
3.42
3.43
3.60
3.61
3.63
3.66
3.67
4.17
4.18
4.20
4.62
4.64
5.51
6.55
6.88
6.90
7.10
7.12
7.15
7.17
7.18
7.26
7.28
7.30
7.32
7.67
7.69
8.35
TBS-protected oxazinin-528 Apr 2011mon5av400#00213C
Acquisition Time (sec) 1.8350 Comment 13C Date 28/03/2011 15:44:12 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 17857.14
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10
Chloroform-d
18.1
118
.60
25.8
1
58.5
961
.45
62.5
8
73.7
976
.19
76.6
877
.00
77.3
2
111.
31
114.
7211
7.05
119.
4912
0.03
122.
3912
4.60
126.
1012
8.24
133.
67
136.
42
157.
79
169.
37
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
38
TBS-protected oxazinin-528 Apr 2011mon5av400#002DEPT
Acquisition Time (sec) 1.2976 Comment DEPT Date 28/03/2011 15:45:30 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 25252.53
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-4.9
7-4
.48
18.6
0
25.8
1
58.5
961
.45
62.5
7
73.7
976
.17
111.
31
114.
71
119.
4912
0.03
122.
3912
4.61
128.
24
TBS-protected oxazinin-628 Apr 2011wed5av500#009alok
Acquisition Time (sec) 3.2768 Comment alok Date 23/03/2011 17:33:42 Frequency (MHz) 500.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 10000.00
Temperature (grad C) 0.000
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
9.717.08 3.17 3.082.26 2.082.052.041.06 1.041.02 1.001.00
TMS
-0.2
1
0.00
0.09
0.90
2.78
2.79
2.80
3.45
3.47
3.48
3.53
3.54
3.57
3.62
4.11
4.12
4.14
4.60
4.62
5.51
6.62
6.81
6.82
7.05
7.06
7.11
7.13
7.17
7.19
7.26
7.29
7.30
7.70
7.72
8.65
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
39
TBS-protected oxazinin-628 Apr 2011wed5av500#00913C
Acquisition Time (sec) 1.1010 Comment 13C Date 23/03/2011 18:14:02 Frequency (MHz) 125.76
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 29761.90
Temperature (grad C) 0.000
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
Chloroform-d
-5.0
0-4
.48
18.0
618
.55
25.7
6
58.6
361
.13
62.5
0
73.7
776
.10
76.7
577
.00
77.2
6
110.
9111
1.49
114.
5611
7.14
119.
4011
9.88
122.
2912
4.94
126.
1612
8.21
133.
47
136.
47
157.
73
169.
67
TBS-protected oxazinin-628 Apr 2011wed5av500#009DEPT135
Acquisition Time (sec) 1.1010 Comment DEPT135 Date 23/03/2011 17:55:36
Frequency (MHz) 125.76 Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 29761.90
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
-5.0
1-4
.48
18.5
4
25.7
6
58.6
261
.13
62.4
9
73.7
776
.09
111.
48
114.
55
119.
3911
9.88
122.
28
128.
21
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
40
oxazinin-528 Apr 2011wed3av400#012VHP
Acquisition Time (sec) 4.0894 Comment Alok Ranjan Date 13/04/2011 22:44:38
Frequency (MHz) 400.13 Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8012.82
Temperature (grad C) 0.000
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
2.102.09 2.05 2.032.02 1.151.10 1.041.031.03 1.000.96
2.84
2.85
2.87
3.47
3.49
3.50
3.52
3.57
3.58
3.60
3.79
3.81
3.86
3.87
4.18
4.19
4.21
4.55
4.56
4.57
4.58
5.29
6.77
6.95
6.95
6.97
7.05
7.14
7.15
7.26
7.27
7.32
7.33
7.35
7.40
7.42
7.58
7.60
9.29
NH
OO
HNO
OH
Synthetic oxazinin-5 (5)(400 MHz, CD3CN, 25 °C)
CN
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
41
oxazinin-516 May 2011wed3av400#01213C
Acquisition Time (sec) 1.2976 Comment 13C Date 14/04/2011 10:21:50 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 25252.53
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10
18.1
5
29.4
2
57.5
4
63.0
363
.07
73.6
473
.94
111.
4911
1.97
114.
6411
8.18
119.
3712
1.83
125.
2712
6.12
128.
10
134.
0713
6.48
157.
99
169.
22
oxazinin-516 May 2011wed3av400#012DEPT
Acquisition Time (sec) 1.2976 Comment DEPT Date 14/04/2011 10:22:24 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 25252.53
Temperature (grad C) 0.000
160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10
18.1
5
29.3
6
57.5
3
63.0
2
73.6
473
.94
111.
49
114.
63
119.
3612
1.83
125.
28
128.
10
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
42
17 May 2011Mon1av400#005Vijendra
Acquisition Time (sec) 4.0894 Comment Vijendra Date 03/05/2011 10:05:10 Frequency (MHz) 400.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8012.82 Temperature (grad C) 0.000
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5
3.06 3.05 2.05 1.201.06 1.021.00 1.00 1.001.00
3.46
3.47
3.49
3.54
3.55
3.57
3.76
3.78
3.79
3.82
3.82
4.47
4.48
4.49
4.50
5.28
5.44
6.79
6.81
7.02
7.04
7.06
7.12
7.13
7.15
7.19
7.21
7.25
7.38
7.40
7.57
7.59
9.30
17 May 2011Mon1av400#005Vijendra
Acquisition Time (sec) 1.3631 Comment Vijendra Date 03/05/2011 10:06:22 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55
57.5
9
63.1
9
73.6
274
.10
111.
5011
1.90
115.
21
117.
35
119.
36
121.
83
125.
3012
6.15
128.
01
132.
17
136.
44
156.
89
169.
30
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
43
17 May 2011Mon1av400#005DEPT
Acquisition Time (sec) 1.3631 Comment Vijendra Date 03/05/2011 10:06:00 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40
57.5
9
63.1
9
73.6
174
.10
111.
51
115.
21
119.
37
121.
83
125.
31
128.
02
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
44
oxazinin-617 May 2011sat5av400#0091H
Acquisition Time (sec) 4.0894 Comment Vijendra Date 30/04/2011 17:36:36 Frequency (MHz) 400.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8012.82 Temperature (grad C) 0.000
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
2.20 2.17 2.162.06 2.05 1.021.02 1.021.01 1.00
2.83
2.84
2.86
3.56
3.57
3.59
3.60
3.61
3.62
3.63
3.91
3.92
4.16
4.17
4.19
4.70
4.71
4.72
4.73
5.38
6.86
6.91
6.93
7.05
7.07
7.09
7.15
7.16
7.23
7.24
7.27
7.29
7.42
7.44
7.61
7.63
9.37
oxazinin-617 May 2011sat5av400#00913c
Acquisition Time (sec) 1.3631 Comment 13c Date 01/05/2011 09:36:18 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10
19.0
4
30.5
9
58.1
8
62.6
564
.18
74.4
675
.25
112.
4711
2.75
115.
5911
8.41
119.
2112
0.19
120.
5912
2.74
126.
2712
7.29
129.
29
135.
3913
7.34
158.
84
170.
06
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
45
oxazinin-617 May 2011sat5av400#009Vijendra
Acquisition Time (sec) 1.3631 Comment Vijendra Date 01/05/2011 09:36:58 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20
19.0
4
30.2
5
58.3
3
62.6
463
.89
74.3
875
.22
112.
40
115.
4211
5.53
120.
2212
0.33
122.
73
126.
24
129.
13
17 May 2011Thu2av400#0091H side product
Acquisition Time (sec) 4.0894 Comment Vijendra Date 13/05/2011 08:57:00 Frequency (MHz) 400.13
Nucleus 1H Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 8012.82 Temperature (grad C) 0.000
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5
6.11 4.002.09 1.031.01 1.00 1.000.98 0.98
3.54
3.55
3.57
3.58
3.59
3.83
4.65
5.38
6.76
6.79
6.87
7.06
7.07
7.09
7.14
7.17
7.23
7.42
7.44
7.62
7.64
9.38
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
46
17 May 2011Thu2av400#00913C side product
Acquisition Time (sec) 1.3631 Comment 13C Date 13/05/2011 08:59:50 Frequency (MHz) 100.61
Nucleus 13C Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46
Temperature (grad C) 0.000
175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55
58.5
6
62.7
8
74.4
675
.56
112.
5611
2.67
116.
1711
8.40
120.
3712
0.48
122.
88
126.
4212
7.47
129.
18
133.
44
137.
49
157.
84
170.
20
17 May 2011Thu2av400#009DEPT, side product
Acquisition Time (sec) 1.3631 Date 13/05/2011 08:57:22 Frequency (MHz) 100.61 Nucleus 13C
Original Points Count 32768 Points Count 32768 Sweep Width (Hz) 24038.46 Temperature (grad C) 0.000
170 160 150 140 130 120 110 100 90 80 70 60 50 40
57.5
1
61.7
4
73.4
274
.52
111.
52
115.
13
119.
3211
9.44
121.
83
125.
38
128.
15
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
47
TBSPROTDED2_1H-4.jdf
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5Chemical Shift (ppm)
3.053.009.463.332.102.061.081.050.991.012.124.100.970.940.830.950.90
-0.1
5
0.02
0.91
1.30
1.31
1.33
2.71
2.73
2.74
4.02
4.04
4.04
4.18
4.20
4.22
4.26
4.29
4.29
4.69
4.69
4.71
4.71
5.39
5.39
6.73
6.75
7.26
7.27
7.29
7.30
7.31
7.34
7.35
8.10
8.12
8.35
8.37
8.54
8.55
9.43
TBSPROTETED2_13C-1.jdf
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.5
4-4
.57
14.1
018
.04
18.5
9
25.6
6
59.4
361
.92
62.3
7
74.3
376
.75
77.0
077
.26
111.
7811
2.93
114.
2111
7.53
122.
2012
3.23
124.
0412
6.41
127.
4913
3.72
135.
7813
8.24
157.
25
162.
29
169.
49
179.
92
NH
HN
O
O
OTBS
CO2Et OCN
(CDCl3, 25 °C)34
NH
HN
O
O
OTBS
CO2Et OCN
(CDCl3, 25 °C)34
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
48
TBSPROTETED2_DEPT135-4.jdf
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8Chemical Shift (ppm)
-5.4
2-4
.46
14.2
2
18.7
2
25.7
8
59.5
562
.04
62.4
9
74.4
6
111.
9011
4.32
122.
3112
3.35
124.
1512
7.61
138.
37
OXAOXADEPNOTE2_1H-4.jdf
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
3.212.115.261.021.002.134.150.970.920.970.940.80
1.20
1.21
1.23
2.76
2.77
2.79
4.01
4.08
4.09
4.10
4.11
4.15
4.16
4.18
4.19
4.66
4.67
4.68
4.69
5.27
6.84
6.85
7.26
7.27
7.27
7.28
7.30
7.32
7.49
7.50
7.51
7.95
7.96
8.25
8.26
8.26
8.68
8.68
10.1
4
NH
HN
O
O
OTBS
CO2Et OCN
(CDCl3, 25 °C)34
(CDCl3, 25 °C)35
NH
HN
O
O
OH
CO2Et OCN
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
49
OXADEPNOTE2_13C-1.jdf
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
14.8
3
19.4
8
59.9
062
.85
64.3
2
73.6
1
113.
6911
5.61
119.
5612
3.07
124.
3612
5.26
127.
8312
8.81
135.
1113
7.57
140.
20
158.
97
163.
72
170.
96
181.
60
NH
HN
O
O
OH
CO2Et OCN
(CDCl3, 25 °C)35
OXADEPNOTE2_DEPT135-3.jdf
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
14.8
4
19.4
8
59.8
962
.87
64.3
0
73.5
8
113.
7011
5.58
123.
0612
4.36
125.
2612
8.80
140.
23
NH
HN
O
O
OH
CO2Et OCN
(CDCl3, 25 °C)35
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
50
OXA_ZININ15_1H-4.jdf
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
2.000.641.001.000.992.020.990.890.931.940.940.951.930.930.930.940.70
2.8
12
.82
2.8
3
3.0
63
.27
3.2
83
.29
3.4
23
.45
3.7
13
.72
3.7
23
.74
3.7
4
4.1
44
.15
4.1
6
4.6
24
.63
5.5
9
6.6
66
.88
6.8
96
.98
7.0
07
.01
7.1
27
.14
7.1
57
.20
7.2
27
.30
7.4
27
.44
7.5
87
.60
9.3
9
OXAZININE18_13C-4.jdf
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
19.0
0
59.8
561
.96
63.8
8
71.0
172
.89
112.
4411
5.43
119.
0912
0.04
120.
3512
2.84
126.
1112
7.48
129.
9613
1.80
137.
43
158.
98
170.
19
O
HN
OH
O
HN OCN
Synthetic oxazinin-1 (1)(500 MHz, CD3CN, 25 °C)
O
HN
OH
O
HN OCN
Synthetic oxazinin-1 (1)(125 MHz, CD3CN, 25 °C)
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OXAZININ15_DEPT135-4.jdf
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
19.0
0
30.2
5
59.8
561
.99
63.9
0
71.0
372
.91
112.
47
115.
43
120.
1212
0.35
122.
85
126.
09
129.
96
OXAZ42_1H-4.jdf
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
2.011.010.800.872.030.870.870.771.861.553.970.800.71
2.79
2.80
2.81
3.25
3.27
3.28
3.29
3.30
3.40
3.42
3.86
4.13
4.14
4.15
4.71
4.73
5.42
6.69
6.90
6.92
7.06
7.07
7.12
7.14
7.30
7.33
7.35
7.38
7.40
7.66
7.67
9.26
O
HN
OH
O
HN OCN
Synthetic oxazinin-4 (4)(500 MHz, CD3CN, 25 °C)
O
HN
OH
O
HN OCN
Synthetic oxazinin-1 (1)(125 MHz, CD3CN, 25 °C)
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OXAZININE47_13C-4.jdf
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
19.2
0
60.7
861
.98
64.1
2
75.6
877
.95
112.
6111
3.41
115.
7011
9.29
120.
4612
0.62
122.
8912
6.39
127.
1612
9.92
132.
07
137.
57
159.
28
170.
79
OXAZININE47_DEPT135-5.jdf
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
19.2
0
60.7
761
.95
64.0
9
75.6
677
.93
112.
61
115.
67
120.
6012
2.89
126.
40
129.
91
O
HN
OH
O
HN OCN
Synthetic oxazinin-4 (4)(125 MHz, CD3CN, 25 °C)
O
HN
OH
O
HN OCN
Synthetic oxazinin-4 (4)(125 MHz, CD3CN, 25 °C)
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OXA26_1H-4.jdf
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
1.351.021.001.000.890.842.000.892.070.930.821.220.57
3.01
3.25
3.39
3.42
3.68
3.68
3.69
3.70
3.71
4.54
4.56
5.55
6.62
6.71
6.73
6.98
7.00
7.06
7.08
7.11
7.12
7.27
7.27
7.40
7.42
7.56
7.58
9.35
OXAXINI29_13C-5.jdf
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
59.9
062
.11
71.2
372
.91
112.
4211
2.48
116.
05
120.
1212
0.39
122.
8812
6.12
127.
5012
9.95
130.
07
137.
48
158.
01
170.
23
O
HN
OH
O
HN OH
Synthetic oxazinin-2 (2)(500 MHz, CD3CN, 25 °C)
O
HN
OH
O
HN OH
Synthetic oxazinin-2 (2)(125 MHz, CD3CN, 25 °C)
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OXAXINI29_DEPT135-4.jdf
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
59.9
062
.08
71.2
072
.89
112.
4711
6.03
118.
3312
0.11
120.
3712
2.86
126.
11
129.
93
Reported CD Spectra of Natural Oxazinin-5 (5):
O
HN
OH
O
HN OH
Synthetic oxazinin-2 (2)(125 MHz, CD3CN, 25 °C)
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CD Spectra of Synthetic Oxazinin-5 (5):
200 220 240 260 280 300 320-20
-15
-10
-5
0
5
10
15
20
25
30
md
eg
Wavelength(nm)
Reported CD spectra of Natural Preoxazinin-7 (7):
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CD spectra of Synthetic Preoxazinin -7 (7):
Reported CD spectra of Natural Oxazinin-6 (6):
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CD Spectra of Synthetic oxazinin-6 (6):
220 240 260 280 300
-4
-2
0
2
4
6
8
10
Elip
ticity
(m
*)
Wavelength(nm)
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Enantiomeric excess of (2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-(tert-
butoxycarbonylamino)-3-hydroxypropanoate (Recemic):
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