Page 1
S1
Supporting Information
Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic
solution
Abdus Salam, Sayan Ray, Md. Abu Zaid, Dileep Kumar and Tabrez Khan
Organic Synthesis Laboratory, School of Basic Sciences, Indian Institute of Technology, Bhubaneswar, Argul, Khurdha 752050, Odisha, India
Email: [email protected]
Table of Contents
i) NMR spectral comparison of synthetic scholarein A with that reported for the natural product S2-S3
ii) Crystal information of compound 32 S3
iii) Copies of NMR spectral data S4-S26
Corresponding author. Tel.: +91-674-713-5164; fax: +0-000-000-0000; e-mail: [email protected]
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
Page 2
S2
Table 1: Comparison of 1H NMR data of natural scholarein A with the synthetic one.
No. of H 1H
data for natural scholarein A
reported in isolation paper1
1H
data reported for synthetic
scholarein A by others2
1H
data for the presently
synthesized scholarein A
CH2(1) or H-C(1)
3.39–3.42 (m) 3.85 – 3.80 (m, 1H),3.68 (dd, J1 = 12 Hz, J2 = 3 Hz, 1H)
3.85 – 3.80 (m, 1H),3.68 (dd, J1 = 12 Hz, J2 = 4 Hz, 1H)
CH2(3) 3.43–3.46(m),3.30–3.33 (m)
3.85 – 3.80 (m, 1H),3.33 (ddd, J = 11.6, 11.6, 2.4 Hz, 1H)
3.85 – 3.80 (m, 1H),3.33 (td, J1 = 11 Hz, J2 = 2 Hz, 1H)
CH2(4) 1.66–1.69(m),1.12–1.15 (m)
1.64-1.49 (m, 1H)1.43-1.32 (m, 1H)
1.56 – 1.49 (m, 1H),1.43 – 1.32 (m, 1H)
H-C(5) 2.16–2.19 (m) 2.26-2.17 (m, 1H) 2.26-2.17 (m, 1H)
CH2(6) 1.58–1.61 (m), 1.32–1.35 (m)
1.85 (ddd, J = 14.4, 6.4, 3.2 Hz, 1H),1.77 (ddd, J = 14.8 Hz, 7.6, 3.2 Hz, 1H)
1.85 (ddd, J1 = 14 Hz, J2 = 6 Hz, J3 = 3 Hz, 1H), 1.77 (ddd, J1 = 14 Hz, J2 = 8 Hz, J3 = 3.0 Hz, 1H)
H-C(7) 3.86–3.88 (m) 4.29-4.25 (1H, m) 4.29-4.25 (1H, m)
H-C(8) 1.45–1.47 (m) 2.10 (ddq, J = 10.8, 6.8, 6.8 Hz, 1H)
2.15 – 2.04 (m, 1H)
H-C(9) 1.69–1.72 (m) 1.64-1.49 (m, 1H)) 1.65 – 1.59 (m, 1H)
Me(10) 0.83 (d, J = 7) 1.01 (3H, d, J = 6.8 Hz) 1.01 (3H, d, J = 7 Hz)
Table 2: Comparison of 13C NMR data of natural scholarein A with the synthetic one.
No. of C
13C
data for natural
scholarein A reported in
isolation paper1
13C
data reported for
synthetic scholarein A by
others2
13C
data for the
presently synthesized scholarein A
CH2(1) or H-C(1)
62.2 67.0 66.9
CH2(3) 61.7 67.4 67.3
CH2(4) 33.2 30.3 30.2
H-C(5) 34.4 34.0 33.8
CH2(6) 40.9 41.7 41.6
H-C(7) 74.7 74.8 74.7
H-C(8) 41.3 37.8 37.6
Page 3
S3
H-C(9) 48.4 43.3 43.2
Me(10) 13.5 11.9 11.7
CRYSTAL INFORMATION OF COMPOUND 32
Compound (32) was crystallized from DCM solvent through slow-evaporation at room temperature. Single crystal X-ray diffraction data were collected on Bruker single-crystal X-ray diffractometer (D8 VENTURE) equipped with a PHOTON 100 CMOS detector. In this case data collection was smooth without any complication and crystal was stable throughout the data collection period. The structure were determined using intrinsic phasing method followed by full-matrix least-squares refinement against F2 using SHELXTL-13. The data of colourless needle-like crystal collected at 110 K using graphite monochromated radiation (λ = 0.71073 Å) : C16H19NO5 , triclinic, P-1, a = 16.691(2), b = 7.895(3), c = 15.590(6) Å, α= 85.482(15), β = 85.127(10) °, γ =68.851(13), V = 764.3(4) Å3 , Z = 2, T = 110(2) K, µ = 0.099 mm-1 , 3863 reflection collected, 2724 independent (R (int) = 0.0837), 3863 observed [I≥2σ(I)], 200 parameters, R indices R1[I≥2σ(I)] = 0.0581 and wR2 = 0.1493, final R (all data) = [I≥2σ(I)] R1 = 0.0838 and wR2 = 0.1723, GOF on F2 = 1.034, max/min residual electron density = 0.26/-0.23 e.A-3 .CCDC 1898028 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
Ref:
1) T. Feng, X.-H. Cai, Z.-Z. Du, X.-D. Luo, Helv. Chim. Acta, 2008, 91, 2247.2) Y. Kawai, S. Megumi, T. Masahiro, Heterocycles, 2012, 86, 1093.
Page 4
S4
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
3.08
1.21
2.49
1.21
1.16
3.31
1.09
1.08
1.06
1.13
1.04
1.00
2.13
2.11
2.00
2.06
-0.0
040.
993
1.01
01.
250
1.25
71.
603
1.85
61.
868
1.87
51.
888
1.89
52.
006
2.01
22.
027
2.03
42.
044
2.05
12.
207
2.22
32.
237
2.33
42.
352
2.46
63.
153
3.17
83.
181
3.20
53.
610
3.62
03.
641
3.65
03.
792
3.82
23.
872
3.88
43.
900
3.91
24.
237
4.24
95.
300
5.41
45.
421
7.26
37.
366
7.38
67.
802
7.82
38.
136
8.14
18.
153
8.15
88.
163
8.26
48.
269
8.27
48.
286
8.29
1
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.1
91
21.6
86
35.7
9538
.136
40.7
3945
.450
66.0
9868
.718
76.6
8277
.000
77.3
1878
.234
78.3
04
123.
569
127.
794
130.
022
130.
558
133.
414
135.
658
145.
326
150.
507
163.
928
19
O
H
HMe
O
OTs
O
O2N
19
O
H
HMe
O
OTs
O
O2N
Page 5
S5
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.42
21.0
7
2.26
2.01
1.02
3.07
0.95
1.00
0.98
1.00
1.90
1.94
1.95
0.92
80.
944
0.95
90.
976
1.00
31.
028
1.62
41.
631
1.64
31.
650
1.65
81.
666
1.67
21.
681
1.69
41.
819
1.83
41.
849
1.86
31.
867
2.18
72.
422
2.43
13.
115
3.13
93.
143
3.16
63.
540
3.54
93.
570
3.57
93.
691
3.69
43.
721
3.72
43.
796
3.80
83.
824
3.83
64.
127
4.13
94.
150
4.16
24.
173
4.17
84.
185
4.19
24.
199
7.26
37.
321
7.34
17.
770
7.77
47.
779
7.79
17.
795
7.80
0
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.1
1512
.281
12.6
4617
.993
18.0
5321
.599
39.3
8239
.771
40.3
5144
.546
66.7
1268
.617
74.3
2376
.683
77.0
0077
.318
79.5
07
127.
766
129.
819
133.
773
144.
884
20
O
H
HMe
TIPSO
OTs
20
O
H
HMe
TIPSO
OTs
Page 6
S6
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
24.5
3
1.14
1.03
1.06
1.04
1.02
1.01
1.00
1.00
0.97
1.01
-0.0
060.
064
1.00
81.
021
1.03
61.
047
1.05
11.
057
1.06
31.
073
1.08
81.
097
1.25
01.
314
1.32
21.
340
1.34
71.
355
1.37
31.
381
1.64
31.
826
1.83
51.
843
1.85
11.
860
1.99
72.
017
2.02
92.
048
2.11
92.
136
2.14
52.
155
2.17
12.
326
2.33
62.
363
2.37
42.
599
2.61
72.
636
2.65
42.
876
2.88
54.
107
4.11
64.
136
4.14
54.
230
4.23
74.
244
4.28
24.
293
4.31
14.
322
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.4
4113
.379
18.0
7618
.106
32.5
1434
.533
41.8
4842
.310
42.4
07
68.6
9576
.201
76.6
8377
.000
77.3
17
173.
634
21
O
H
HMe
TIPSOO
21
O
H
HMe
TIPSOO
Page 7
S7
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.29
2.11
1.05
1.07
1.04
1.04
1.00
0.98
1.98
1.00
-0.0
060.
064
0.07
31.
071
1.08
91.
248
1.41
21.
420
1.43
71.
446
1.92
32.
026
2.04
62.
060
2.08
02.
157
2.35
42.
364
2.39
22.
401
2.61
42.
632
2.65
22.
670
4.13
04.
134
4.13
74.
159
4.16
74.
297
4.30
74.
326
4.33
6
5.30
0
7.26
3
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
12.6
39
32.6
2434
.471
41.4
1541
.543
41.6
28
68.5
2575
.546
76.6
8377
.000
77.3
18
173.
480
isoboonein (2)
O
OH
HMe
HO
isoboonein (2)
O
OH
HMe
HO
Page 8
S8
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.21
1.40
1.13
2.59
2.12
1.04
3.15
1.20
1.04
1.06
1.03
1.00
2.03
1.96
-0.0
040.
922
0.93
81.
119
1.16
01.
174
1.18
71.
251
1.39
01.
401
1.57
31.
581
1.58
81.
598
1.60
51.
613
1.62
31.
639
1.79
81.
813
1.83
11.
845
1.87
31.
896
2.12
12.
128
2.14
22.
150
2.41
22.
448
3.17
73.
200
3.20
63.
228
3.52
03.
530
3.55
03.
560
3.62
03.
628
3.65
03.
658
3.80
73.
818
3.83
53.
846
4.25
14.
262
4.27
34.
284
4.29
54.
306
7.26
17.
332
7.35
37.
793
7.81
4
0102030405060708090100110120130140150160170180190200f1 (ppm)
19.7
0821
.638
26.4
6931
.336
33.4
04
43.1
4247
.825
66.6
9168
.462
76.6
8377
.000
77.3
1877
.978
127.
807
129.
832
133.
875
144.
851
22
O
H
HMe
OTs
22
O
H
HMe
OTs
Page 9
S9
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.16
2.54
3.36
1.08
1.06
2.04
1.03
1.00
1.02
61.
028
1.04
01.
111
1.12
41.
141
1.15
41.
177
1.18
81.
198
1.21
01.
218
1.23
1
1.77
91.
795
1.81
21.
823
1.85
71.
973
1.98
72.
306
2.32
72.
533
2.55
12.
576
2.58
6
4.05
64.
067
4.08
54.
096
4.22
94.
240
4.25
84.
269
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
18.6
30
33.3
3134
.544
34.7
3434
.755
37.4
3144
.527
68.8
8976
.681
77.0
0077
.317
173.
616
7-epi-boschnialactone (3')
O
OH
HMe
7-epi-boschnialactone (3')
O
OH
HMe
Page 10
S10
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.55
2.79
1.34
3.37
1.24
1.05
1.08
1.10
1.04
1.00
-0.0
041.
069
1.08
51.
193
1.19
71.
209
1.21
31.
223
1.22
71.
239
1.24
31.
249
1.26
71.
397
1.40
51.
413
1.42
01.
428
1.43
71.
452
1.60
91.
848
1.86
41.
871
1.87
91.
888
1.89
91.
903
1.91
61.
928
1.93
91.
941
1.95
21.
964
2.09
52.
098
2.10
32.
115
2.11
82.
130
3.13
33.
154
4.02
54.
038
4.05
44.
067
4.16
24.
172
4.19
04.
201
5.46
05.
463
5.46
76.
036
6.03
96.
043
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
18.9
37
29.7
0833
.932
34.9
5636
.893
41.8
9445
.402
68.2
6676
.715
77.0
3377
.350
124.
677
140.
445
169.
429
teucriumlactone (4)
O
OH
HMe
teucriumlactone (4)
O
OH
HMe
Page 11
S11
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
5.73
2.96
4.41
0.98
1.02
0.98
1.00
0.98
31.
010
1.02
41.
100
1.11
71.
146
1.16
21.
279
1.74
01.
753
1.78
91.
804
2.55
42.
570
2.58
82.
650
2.66
72.
683
2.70
0
4.12
44.
153
4.22
04.
225
4.24
94.
254
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.5
85
18.2
27
29.6
7234
.040
37.1
4937
.798
41.0
4545
.363
67.8
13
76.6
8177
.000
77.3
18
176.
138
iridomyrmecin (1)
O
OMe
H
HMe
iridomyrmecin (1)
O
OMe
H
HMe
Page 12
S12
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.34
1.03
1.16
1.15
3.61
1.05
1.04
3.37
1.00
1.12
2.33
2.29
-0.0
141.
663
1.93
01.
934
2.19
22.
198
2.20
32.
209
2.21
42.
243
2.24
82.
254
2.35
42.
364
2.37
02.
380
2.38
72.
436
2.59
63.
639
3.65
13.
667
3.67
83.
693
3.70
3
4.30
24.
313
4.32
04.
330
4.33
84.
349
5.29
8
7.26
07.
320
7.34
07.
771
7.79
27.
801
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.6
06
21.6
02
33.4
98
41.8
6946
.140
66.9
3167
.728
76.6
8277
.000
77.3
1877
.991
124.
596
127.
727
129.
801
133.
783
140.
970
144.
796
23
O
H
HMe
OTs
23
O
H
HMe
OTs
Page 13
S13
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.33
1.37
1.21
2.27
2.09
2.20
1.00
-0.0
05
0.87
5
1.25
01.
280
1.28
91.
690
1.69
5
2.35
42.
365
2.39
12.
402
2.62
12.
638
2.65
82.
675
2.94
42.
956
2.96
5
4.23
04.
241
4.25
94.
263
4.27
04.
298
4.30
84.
328
4.33
7
5.42
2
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.5
17
29.7
1132
.701
35.8
0239
.626
47.3
76
67.4
94
76.7
1777
.034
77.3
52
126.
779
136.
721
173.
378
24
O
H
HMe
O
24
O
H
HMe
O
Page 14
S14
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.02
1.74
1.34
1.40
1.53
1.18
1.51
1.19
2.34
1.12
1.00
1.01
61.
034
1.24
11.
253
1.27
31.
299
1.31
61.
328
1.34
51.
359
1.37
51.
470
1.48
71.
496
1.50
21.
508
1.51
91.
705
1.71
11.
720
1.72
61.
736
1.74
21.
838
1.86
01.
867
1.87
71.
889
1.89
32.
249
2.27
62.
291
2.31
82.
320
2.34
02.
358
2.40
02.
414
2.42
22.
436
2.57
12.
589
2.59
52.
600
2.61
32.
618
2.62
12.
630
4.09
14.
114
4.12
04.
142
4.19
74.
211
4.22
64.
240
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.6
41
29.6
3932
.806
32.8
6934
.876
35.0
7137
.335
39.6
70
67.5
03
76.6
8277
.000
77.3
17
173.
819
boschnialactone (3)
O
OH
HMe
boschnialactone (3)
O
OH
HMe
Page 15
S15
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.78
1.30
1.22
1.15
1.15
1.06
1.10
1.11
1.00
-0.0
050.
875
1.25
01.
280
1.73
51.
740
1.74
51.
750
2.04
32.
125
2.13
12.
136
2.14
22.
168
2.17
42.
179
2.18
52.
325
2.34
02.
371
2.38
52.
647
2.65
32.
659
2.66
72.
673
2.67
92.
690
2.69
62.
702
2.70
92.
716
2.72
22.
913
2.93
92.
958
2.98
43.
052
3.05
83.
067
3.07
23.
078
3.08
43.
087
3.09
33.
098
3.10
43.
113
3.53
33.
563
3.96
43.
994
5.62
85.
633
5.63
75.
643
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.4
16
29.6
7437
.520
37.6
6737
.862
64.0
84
76.6
8377
.000
77.3
18
100.
785
130.
344
137.
550
177.
118
25
O
OH
OHMe
25
O
OH
OHMe
Page 16
S16
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.88
2.57
1.40
1.52
1.20
1.13
2.29
1.04
1.00
1.25
31.
373
1.55
91.
568
1.57
41.
577
1.58
51.
592
1.59
91.
603
1.60
61.
615
1.63
21.
640
1.65
51.
671
1.68
01.
687
1.69
61.
712
1.77
11.
780
1.78
61.
797
1.80
21.
812
1.82
81.
956
1.96
11.
965
1.97
11.
977
1.98
11.
986
1.99
21.
996
2.41
82.
437
2.45
22.
472
2.55
42.
574
2.58
12.
602
2.60
92.
617
2.63
72.
652
4.29
84.
313
4.32
84.
343
4.44
94.
469
4.47
94.
498
7.26
3
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
14.1
0922
.679
28.0
0629
.348
29.6
8330
.790
31.9
1134
.918
35.1
7341
.914
46.0
34
66.5
5776
.683
77.0
0077
.318
79.8
66
173.
648
7-epi-argyol (5')
O
OH
HHO Me
7-epi-argyol (5')
O
OH
HHO Me
Page 17
S17
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.88
3.52
1.16
2.30
1.12
1.07
1.15
1.11
1.00
-0.0
290.
043
1.18
71.
202
1.22
51.
252
1.25
71.
634
1.78
22.
146
2.18
92.
349
2.36
12.
372
2.38
22.
396
2.41
12.
700
2.70
52.
719
3.01
6
3.90
03.
929
3.95
84.
388
4.40
34.
416
4.43
1
5.38
6
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.0
3314
.681
38.8
0738
.920
40.9
0648
.070
68.7
7176
.682
77.0
0077
.318
126.
190
136.
727
175.
827
26
O
H
HMe
OMe
26
O
H
HMe
OMe
Page 18
S18
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5
f1 (ppm)
2.99
3.73
2.47
1.11
2.08
1.02
1.00
0.95
1.01
-0.0
120.
058
1.16
91.
185
1.36
91.
677
1.68
61.
694
1.70
61.
719
1.73
21.
807
1.81
21.
822
1.82
72.
000
2.00
92.
018
2.02
02.
031
2.28
02.
298
2.47
02.
481
4.30
94.
326
4.33
84.
355
4.38
84.
417
4.44
6
5.29
6
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
13.5
85
27.7
3130
.084
38.9
8442
.464
42.5
5846
.704
65.7
67
76.6
8277
.000
77.3
1779
.579
176.
628
scabrol A (6)
O
OH
HHO Me
Me
scabrol A (6)
O
OH
HHO Me
Me
Page 19
S19
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
4.13
3.34
2.51
2.24
4.16
1.04
1.00
-0.0
040.
066
1.23
01.
244
1.28
51.
547
1.56
01.
574
1.58
71.
609
1.72
21.
735
1.74
41.
756
2.24
72.
267
2.27
72.
301
2.31
62.
324
2.34
52.
359
2.37
62.
391
3.83
33.
861
3.86
33.
892
4.25
44.
269
4.28
24.
296
5.30
0
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.3
47
23.6
14
29.7
86
37.7
0939
.112
41.6
89
49.1
60
66.7
50
76.6
8377
.000
77.3
1880
.535
175.
576
7-epi-scabrol A (6')
O
OH
HHO Me
Me
7-epi-scabrol A (6')
O
OH
HHO Me
Me
Page 20
S20
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.08
3.05
1.03
2.17
1.04
1.04
0.95
1.01
1.00
-0.0
11
1.11
71.
134
1.24
31.
412
1.95
71.
990
2.09
32.
117
2.12
12.
142
2.15
22.
157
2.15
92.
186
2.49
0
3.43
33.
436
4.33
24.
361
4.38
94.
486
4.50
44.
514
4.53
2
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
13.3
2716
.591
31.5
59
39.0
0641
.515
41.7
72
65.5
1467
.045
67.6
6076
.683
77.0
0077
.318
176.
265
27
O
H
HMe
OMe
O
27
O
H
HMe
OMe
O
Page 21
S21
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.09
3.18
1.10
1.16
1.10
2.07
0.95
1.04
1.00
-0.0
06-0
.005
1.18
91.
205
1.24
81.
398
1.61
71.
621
1.63
51.
639
1.65
31.
657
1.99
62.
263
2.28
02.
288
2.30
42.
522
2.54
42.
558
2.57
9
3.40
9
4.03
64.
064
4.09
54.
283
4.29
54.
310
4.32
2
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
14.3
4915
.270
29.6
6735
.812
39.4
5739
.520
43.4
65
64.4
9864
.730
65.8
5776
.683
77.0
0077
.318
174.
722
28
O
H
HMe
OMe
O
28
O
H
HMe
OMe
O
Page 22
S22
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.05
3.22
2.27
1.51
2.38
1.00
1.01
1.16
-0.0
100.
870
1.16
31.
179
1.19
71.
214
1.24
31.
252
1.27
61.
304
1.35
71.
941
1.95
21.
961
1.97
12.
192
2.42
82.
444
2.45
82.
469
2.47
42.
486
2.49
82.
515
3.97
03.
980
3.99
14.
331
4.34
94.
360
4.37
74.
393
4.42
24.
451
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
13.5
96
22.3
46
29.6
51
37.6
8238
.960
39.5
2544
.043
65.6
15
76.6
8277
.000
77.3
1780
.682
81.2
13
176.
715
patriscabrol (7)
O
OH
HHO Me
Me
HO
patriscabrol (7)
O
OH
HHO Me
Me
HO
Page 23
S23
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.66
22.3
3
1.57
1.16
1.48
2.10
1.20
1.05
1.03
1.07
2.14
1.00
-0.0
030.
068
0.98
10.
998
1.00
71.
020
1.03
41.
051
1.05
61.
068
1.08
51.
093
1.10
71.
251
1.28
21.
290
1.33
11.
368
1.37
91.
410
1.48
91.
497
1.50
41.
650
1.65
71.
667
1.67
51.
776
1.78
81.
793
1.80
32.
012
2.02
92.
045
2.05
52.
163
2.17
93.
302
3.30
83.
330
3.33
63.
358
3.36
53.
636
3.64
53.
666
3.67
53.
758
3.76
43.
775
3.78
63.
794
3.81
24.
390
4.40
34.
405
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.3
9812
.972
18.0
8918
.141
29.9
0033
.495
38.3
7842
.748
43.8
15
67.0
1267
.308
74.8
4176
.683
77.0
0077
.318
29
O
H
HMe
TIPSO
29
O
H
HMe
TIPSO
Page 24
S24
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.19
2.44
4.46
0.92
1.12
1.03
0.98
1.00
0.99
1.91
-0.0
031.
052
1.06
91.
252
1.29
11.
364
1.37
61.
386
1.39
81.
407
1.41
11.
420
1.59
91.
608
1.61
51.
623
1.63
21.
640
1.65
81.
669
1.68
41.
694
1.70
31.
710
1.72
01.
970
1.97
81.
986
1.99
52.
080
2.18
02.
201
2.21
42.
221
2.23
63.
358
3.36
53.
386
3.39
33.
413
3.42
03.
595
3.60
53.
625
3.63
53.
764
3.77
13.
794
3.80
13.
815
3.82
73.
831
3.83
73.
848
3.85
43.
866
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
16.6
73
29.6
7629
.883
33.9
6339
.995
42.0
3545
.096
66.7
9067
.140
76.6
8277
.000
77.3
1780
.777
31
O
H
HMe
HO
31
O
H
HMe
HO
Page 25
S25
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
3.14
1.12
3.26
1.07
1.03
1.06
1.04
1.09
1.06
1.07
2.12
1.00
1.98
1.99
-0.0
021.
042
1.05
91.
472
1.48
31.
574
1.58
21.
592
1.59
51.
763
1.96
31.
973
1.98
11.
992
2.00
02.
048
2.05
52.
065
2.07
22.
404
2.42
12.
433
2.43
82.
450
3.33
53.
341
3.36
43.
370
3.39
33.
399
3.69
73.
706
3.72
73.
736
3.85
33.
866
3.87
13.
882
3.90
05.
542
5.55
05.
559
5.56
75.
575
7.26
38.
167
8.17
28.
177
8.18
98.
194
8.20
08.
270
8.27
58.
280
8.29
28.
297
8.30
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
12.2
67
29.7
4634
.041
36.6
2639
.258
44.3
22
66.4
9867
.151
76.6
8377
.000
77.3
1779
.266
123.
539
130.
568
136.
081
150.
476
164.
229
32
O
H
HMe
OO
O2N
32
O
H
HMe
OO
O2N
Page 26
S26
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.33
2.08
1.21
1.10
1.14
1.05
1.06
1.07
1.10
2.14
1.00
-0.0
021.
002
1.02
01.
252
1.33
51.
352
1.35
81.
364
1.37
01.
387
1.39
81.
415
1.42
71.
503
1.51
11.
519
1.53
71.
553
1.62
31.
640
1.64
61.
749
1.76
91.
778
1.78
51.
797
1.80
51.
823
1.83
01.
839
1.84
62.
071
2.08
82.
103
2.11
72.
208
2.21
73.
295
3.30
13.
324
3.33
03.
352
3.35
93.
659
3.66
83.
689
3.69
83.
804
3.80
93.
820
3.83
93.
849
4.26
04.
268
4.27
54.
283
7.26
3
0102030405060708090100110120130140150160170180190200f1 (ppm)
11.7
04
30.1
5833
.832
37.5
7941
.536
43.1
33
66.8
6267
.241
74.6
5576
.682
77.0
0077
.317
Scholarein A (9)[Proposed structure]
O
H
HMe
HO
Scholarein A (9)[Proposed structure]
O
H
HMe
HO
![PSLC Spectral Database. - Jcamp viewer nmr data processing · 2009. 5. 24. · Printed: Sunday, May 24, 2009 1:08:47 PM Devin Chem 325[NMR FID{^1H}] Printed: Sunday, May 24, 2009](https://static.documents.pub/doc/80x56/60afc0b9cbb0d2558460adf9/pslc-spectral-database-jcamp-viewer-nmr-data-processing-2009-5-24-printed.jpg)
