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JACS: 1984 Year in Review
1
Jun ShiBaran Group Meeting3/28/2007
A Survey of Papers with a Focus on Synthetic Organic
Chemistry
Statistics for JACS 1984:
Total Number of Papers: 2,215Papers focused on synthesis:
224Total synthesis papers: 52
Top Organic Chemistry Authors:
L. A. Paquette: 14M. J. Dewar: 12E. J. Corey: 9B. M. Trost: 8H.
C. Brown: 7J. K. Stille: 4
Nature Products discussed in part or full
O
O
HOOH
(±) -Talaromycin B
O
HO
HO
O
(±)-VerrucarolOH
HO
OH
O
O
HN
NH2HClO
(+)-Actinobolin
HN NH
NH
(-)-Ptilocaulin
HN
NH
OO
OH
HO
HO
Me
HO H
O
(+)-Bicyclomycin
O
O
O H
H
CH3
O
O
H
H
MeO2C
(+)-Phyllanthocin
O
OO
O
OO
(±)-Gnididione (±)-Isognidione
OO
MeO
OH
N
OH
OO
MeO
O
NMe
OH
HaemathidinePretazettine
NH
N
O
H
HH
O
O
H
!"Cyclopiazonic Acid
O
O
O
(±)-Hibiscone C
HN
N N
NHHN
NH
HO
HO
HO
NH2
O
(±)-Saxitoxin
HO
OH
(±)-Poitediol
O
O(±)-Dehydrocostus Lactone
O
O
O
(±)-Estafiatin
OH
O
O
O
O
(+)-Coriamyrtin
O
OHO
O
O
(+)-Dihydrocompactin
O
N
n-C5H11
H HN
HN
O
Anhydrocannabisativene
H
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JACS: 1984 Year in Review
2
Jun ShiBaran Group Meeting3/28/2007
NOC Approach to Spiroketals. A Total Synthesis of (±)
-Talaromycin B
Alan P. Kozikoweski and James G. Scripko; J. Am. Chem. Soc.
1984, 106, 353-355
O O O O
N
H
OH
+ O
O
N O
O
O
O
O
HOOH
OH
O
O
HOOH
(±) -Talaromycin B
NaOCl, Et3N
H2, Raney Ni
Then, MeOHAmberlyst 15
A Tandem Cycloaddition-Ene Strategy for the Synthesis of
(±)-Verrucaroland (±)-4,11-Diepi-12,13-deoxyverrucarolBarry M.
Trost, Patrick G. McDougal and Kenneth J. Haller;J. Am. Chem. Soc.
1984, 106, 353-355
Cl
OH
O
O
TsOH, !
ClO
O
O
O
MeO3C
OTMS
!
O
HO
OTMSMeO2C
O
O
OTMS
O
1.NaBH4
2. 470ºC
O
O
OTMS
O
Br
bromine-dioxanecomplex
TBAF
O
O
O
O
O
HO
HO
O
(±)-Verrucarol
steps
steps
Stereocontrolled Total Synthesis of (+)-Actinobolin by an
Intramolecular Diels-Alder Reaction of a Chiral Z Diene Derived
from L-ThreonineMasato Yoshiok, Hisao Nakai, and Masaji Ohno, J.
Am. Chem. Soc. 1984, 106, 1133-1135
N
O
Ph
NH
OMe Ph
O
EtO2C
O
NH
O
OTHP
CO2H
NH
O
OH
CO2Me
O
NPMS
O
O2CPh
HO
OH
PhSe
HO
OH
PhSe
O
O
NHPMS
OH
HO
OH
O
O
HN
NH2HClO
(+)-Actinobolin
1. 1N HCl
2.
1. heat2. NaOH3. CH2N24. DHP,5. NaOH
NaOMe
1. KMnO4, CH2N22. DBU
EtO2C
Cl
O
1. I2, NaHCO3, H2O2. NaOH, H2O3. CH2N24. TsOH
1. HCO2H,2. Me2C(OMe)23. DHP, H+
4. LAH, 5. TsCl, PhSeSePh6. BuLi, PMS-Cl7. TsOH
1. O3, Py2. O3, MeOH DMS3. HF4. Ala, DCC
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JACS: 1984 Year in Review
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Jun ShiBaran Group Meeting3/28/2007
Total Synthesis of (-)-PtilocaulinWilliam R. Roush and Alan E.
Walts, J. Am. Chem. Soc, 1984, 106, 721-723
O O O
CHO
N OPh
NH OPhHN NH
NH
(-)-Ptilocaulin
Total Synthesis of (-)-PtilocaulinBarry B. Snider and William C.
Faith, J. Am. Chem. Soc, 1984, 106, 1443-1445
4 stepsTiCl4
allytrimethylsilane
PhCH2NHOH
1. Zn, AcOH
2. Jone's reagent
1. Pd black
OO
OO
OHN NH
NH
(-)-Ptilocaulin
O
O
MgBr
CuBr(CH3)SHCl
guanidine
Stereocontrolled Total Synthesis of (±)!and (+)-Bicyclomycin:
New Carbon-Carbon Bond-Forming Reactions on Electrophilic Glycine
Anhydride DerivativesRobert M. Williams, Robert W. Armstrong, and
Jen-Sen DungJ. Am. Chem. Soc, 1984, 106, 5748-5750
BnN
NBn
O
O
BnN
NBn
O
O
S
S
N
N
BnN
NBn
O
O
S
N
OO
BnN
NBn
O
O
S
N
HOHO
BnN
NBn
O OH
H
O
O
BnN
NBn
O
H
O
O
OH BnN
NBn
O
OOH
O
O
Me
HO H
O
HN
NH
O
OOH
HO
HO
Me
HOH
O
(+)-Bicyclomycin
1.NBS, CCl4
2. NaS(py)
1eq. AgOTf
O
OTMS
LAH 1eq. AgOTf
n-BuLi
O
O CHO
1.TFAA
2. CAN
1. LDA,P(OEt)3Cl
o
2. 9-BBN3. Li, EtNH2, t-BuOH4. PCC
2. GDMP1. MsCl NaBH3SePh H2O2
2. 1.5 eq n-BuLi, 2 eq HMPA 2eq (Me3N)3P, O2
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JACS: 1984 Year in Review
4
Jun ShiBaran Group Meeting3/28/2007
Total Synthesis of (+)-PhyllanthocinD. R. Williams and Sing-Yuen
Sit, J. Am. Chem. Soc., 1984, 106, 2949-2954
O
HH
CO2Et
EtO2C steps
H
H3C
H
OSitBuPh2
OS
SLi
MEMCl
SS
OTBDPS
OMEM
H3C H
BnO
OTBDPS
O
H
HMPA, t-BuLi, then TBAF
OH
BnOOH
OH
SS OMEM
CH3
1.HgCl2, HgO
OBnO
O
2. H2CrO4
O CH3
OMEM
O
O
O H
H
CH3
O
O
H
H
MeO2C
(+)-Phyllanthocin
O
MeO2C
CO2Me
1. 2eq LiCH2NC2. NaH, MeI3.HOCH2CH2OH, H
+
4. PhN(Me)3+Br_5. DBU, Heat6. DIBAL N
O
CHO
O
O
N
O
O
O
OH
Heat
O
O
OO
O
OO
O
OO
(±)-Gnididione
(±)-Isognidione
Bis Heterannulation 7. Total Synthesis of (±)-Gnididione and
(±)-IsognidionePeter A. Jacobi and Harold G. Selnick, J. Am. Chem.
Soc., 1984, 106, 3240-3245
Total Syntheses of the Amaryllidaceae Alkaloids
(±)-Haemanthidine and (±)-PretazettineStephen F. Martin and Steven
Davidsen, J. Am. Chem. Soc., 1984, 106, 6431-6433
O
O
N
CHPh
O OCHO
OO
ON
CO2C3H5
OCOtBu
OO
ON
CO2C3H5
OCOtBu
OO
O
OCOtBu
NMe
1. n-BuLi2.CHOCH2NMeCO2C3H53. Pivaloyl Chloride4. HCl
pyrrolidineAcOH-MeOH
1. DIBAL, MeOH2. Pt, O23. CH3CO2CHO
1. H2/Pd/C2. Jones, CH2N23. ZnBr4. (CH3)2SOCH25. Cinnamoyl
chloride
1. LiCCMe2. Swern3.
MgBr
1. PhNMe3Br32. DBU3. Pd(PPh3)4
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JACS: 1984 Year in Review
5
Jun ShiBaran Group Meeting3/28/2007
OO
MeO
OCOtBu
NCHO
OO
MeO
OCOtBu
N
OH
OO
MeON
OH
OO
MeO
O
NMe
OH
HaemathidinePretazettine
POCl3, heatLiOH
MeIMeOH
Total Synthesis of the Unique Mycotoxin !"Cyclopiazonic Acid
(!CA): An UnusualDimethylzinc-Mediated Replacement of a Phenylthio
Substituent by a Methyl Groupand a Contrathermodynamic Raney Nickel
Desulfuriztion ReactionAlan P. Kozikowski and Michael N. Greco, J.
Am. Chem. Soc., 1984, 106, 6873-6874
NTs
CHO
NH
O
O CO2Et
NHAc
1. ClCO2Et, Et3N2. HCl3. MeSiI, HN(SiMe)2 PhSCl
NCO2Et
CO2Et
NHAc
O
SPh
NCO2Et
CO2Et
NHAc
O
1. DBU, BuOH
2. H2, Raney Ni
NCO2Et
NAc
SPh
CO2Et
NCO2Et
NAc
CO2Et
PhSH, Mg(OTf)2 Me2Zn, CHCl3
1. Et3O+BF4
-, Na2CO3, HOAc
2.
O
O
NCO2Et
N
O O
CO2Et
NH
N
O
H
HH
O
O
H
NaOMe, MeOHPhH
Et3N, #
NH
N
O
H
HH
O
O
H
!"Cyclopiazonic Acid
Intramolecular [2+2] Photocycliztions. 2. Total synthesis of
(±)-Hibiscone C (Gmelofuran)Emil R. Koft and Amos B. Smith, III J.
Am. Chem. Soc., 1984, 106, 2115-2121
O OH
HhvO
H
O
H
O O
HO HO
+O3, Ph3P
TsOH, refluxO
OO
O
steps O
(±)-Hibiscone C
OH
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JACS: 1984 Year in Review
6
Jun ShiBaran Group Meeting3/28/2007
Total Synthesis of (±)-SaxitoxinPeter A. Jacobi, Michael J.
Martinelli, and Solvenko PolancJ. Am. Chem. Soc., 1984, 106,
5594-5598
HN
NH
O HN
HN Ph
S S
BF3•Et2O
MeOCHCO2Me
HN
NH
O N
N Ph
S S
H CO2Me
HN
NH
O N
N Ph
S S
H CH2OH
NaOMeNaBH4
OOO
BH3•DMSHN
NH
O N
N Ph
S S
H CH2OH
HN
NH
O N
N
S S
H CH2OH
OPh
S
1. Pd, HCO2H2. PhOCCl
S
Na, NH3
HN
NH
N
NHO
S
SS
H CH2OH
1. Ac2O/Py
2. Et3O+BF4
-
KHCO3
N
NH
N
NEtO
SEt
SS
H CH2OAc
EtCO2-NH4
+
130°C
N
NH
N
NHN
NH
SS
H CH2OH HN
NH
N
NHHN
NH
HOOH
HO
NH2
O
(±)-Saxitoxin
Total Synthesis of (±)-Poitediol and (±)-4-EpipoitediolRobert C.
Gadwood, Renee M. Lett and Jane E. WissingerJ. Am. Chem. Soc.,
1984, 106, 3869-3870
O
MeO
OHMeO
steps O
BF3•Et2O
O
LiCCHthen !
1. MeLi, -78°C
2. PCC3. LiMe2Cu, Me2S
O stepsHO
OH
(±)-Poitediol
Total Synthesis of Guaianolides: (±)-Dehydrocostus Lactone and
(±)-EstafiatinJames H. Rigby and JoAnn Zbur Wilson, J. Am. Chem.
Soc., 1984, 106, 8217-8224
O
MgBr O
O
O
O
O
O
OMe
1. NaBH42. TFA
3. BF3•Et2O
1. Li/CH2NH2, reflux
2. DIA, MEMCl
OMe
MEMO
1. m-CPBA
2. dilithioacetate
OMe
MEMO
O
O
1. TMSCl, NaI2. swern
3. Ph3P=CH2
O
O
LDA,+NH2=CH2
O
O
O
O
O
O(±)-Dehydrocostus Lactone
BF3•Et2OO
(±)-Estafiatin
mCBPA
1. NBS, wet, CH3CN2. chlorosulfoyl isocyanate
OH
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JACS: 1984 Year in Review
7
Jun ShiBaran Group Meeting3/28/2007
Stereocontrolled Total Synthesis of (-)-Picrotoxinin and
(+)-Coriamyrtin via a Common Isotwistane IntermediateKiyoyuki
Yamada etc, J. Am. Chem. Soc., 1984, 106, 4547-4552
OO
O
CO2Me
1. mCPBA2. DBU
OO
O
CO2Me
OHHO
OH
CO2MeO1. aq. AcOH2. Et2NH
O
OMe
1. HO(CH2)2OH, TsOH2. LAH, TBDMS3. PCC4. MeI, NaH
OTBDMS
OO
O
OMe
OTBDM
OO
LDAMoO5HMPAPy O
O
OMe
O
O
OTBDMS
HO OMe
OH
1. MeLi2. Pb(OAc)23. t-AmOK
1. PhSONMeCH2Li2. Al(Hg)3. Ph3P=CH24. HCl5. Na
1. CSCl, Py2. NaH, DME
3. NBS, -78°C
O
OBr
NBS, RT
O
OBr
O
OBr
Br
Br
O
OBr
OH
1. t-BuOK2. NBS,H2o
Br
1. t-BuOK2. mCPBA
O
OBr
O
O
1. RuCl3, NaIO42. Zn OH
O
O
O
O
(+)-Coriamyrtin
+
Total Synthesis of (+)-DihydrocompactinYuh-Lin Yang, Sukumar
Manna and J.R.Falck, J. Am. Chem. Soc., 1984, 106, 4547-4552
SO2PhO
OOSO2Ph
OO
O
1. LHMDS2. CH2N23. Al(Hg)
4. NaOMe
CO2MeOHO
OO
1. (HOCH2)2 TsOH2. LAH
1. Me3SiCl, NaI2.PhSO2-Amberlyst 26-A3. (HSCH2)2CH2,
BF3•Et2O
PhO2S
SS
O
OMeTBDPSO
I
O
OMeTBDPSO
SS
O
OHO
O
O
(+)-Dihydrocompactin
steps
Total Synthesis of AnhydrocannabisativeneThomas R. Bailey, Ravi
S. Garigipati, Judith A. Morton and Steven M. WeinrebJ. Am. Chem.
Soc., 1984, 106,3240-3245
Methyl glyoxylate
O
H2N O
O
HN
CO2Me
O
n-C5H11 n-C5H11
OAc
Hunig's Base
O
N
CO2Me
O
n-C5H11
H
HO
O
O
O
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JACS: 1984 Year in Review
8
Jun ShiBaran Group Meeting3/28/2007
1. NaOH, MeOH2. (COCl)2,3. CH2N24. Ag2O/MeOH
O
N O
n-C5H11
HCO2Me
OTBDMS
NH
n-C5H11
HCO2Me
1. Ba(OH)2 !
2. SOCl2/MeOH TBDMSCl
HO NHTs
OTBDMS
N
n-C5H11
HCO2Me
NHTs 1. LiOH, MeOH
2. 4-aminobutanol DMF
OTBDMS
N
n-C5H11
H TsN
HN
O
3. K2CO3, reflux
1. Na/NH32. BF3•Et2O
3. Jones reagent
O
N
n-C5H11
H HN
HN
O
Anhydrocannabisativene
Other Total Syntheses Published In 1984 in JACS
O
n-C5H11
CO2CH3
AcO
OAc
(±)-ClavulonesE. J. Corey, 3384Logic: 303-304
O
O
O
HybridalactoneE. J. Corey, 2735Logic: 307-309
NH
O
OH
OAc
O
Ph
Cytochalasan DE. Vedejs, 4617see groupmeeting"Cytochalasan"
O O
Me
H
HO OH
O
MeOMe
O
Me
Me
(±)"AsteltoxinS. L. Schreiber, 4186see Classics I, Chapter
20
N
OH
OH
CH3
OH
Pumiliotoxin BL. E. Overman, 4192See
groupmeeting"Indolizidine"
Me
Me
O
O
O
(±)-QuadroneS. D. Burke, 4558see groupmeeting"Quadrone"
COOH
OH
OH
5, 15-DiHETEK. C. Nicolaou, 5734
COOH
OH OH
Leukotriene B4K. C. Nicolaou, 3548
O
OO
O
(±)"AvenaciolideS. L. Schreiber, 7200
O
MeO
OO
OMe
OHH
dl-QuassinP. A. Grieco, 3539
O
O
O
OH
COOH
(±)-Nanaomycin AL. S. Liebeskind, 4181
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JACS: 1984 Year in Review
9
Jun ShiBaran Group Meeting3/28/2007
MethodologySilane Chemistry:
N-Trimethylsilyl Imines: Applications to the Synthesis of
!-LactamsDeok-Chan Ha, David J. Hart and Teng-Kuei YangJ. Am. Chem.
Soc., 1984, 106, 4819-4825
R NSiMe3
1.OLi
OEt
2. HCl, H2O NHO
R
Regiochemistry of Alkenylsilyl and Alkenyldisilanyl Radical
CyclizationsThomas J. Barton and Anthony RevisJ. Am. Chem. Soc.,
1984, 106, 3802-3805
The Michael Reaction of Silyl Enol Ethers or Ketene Silyl
Acetals with ConjugatedNitro Olefins Acitivated by the Lewis Acid:
New Synthesis of 1, 4-Diketones and "#Keto EstersAkira Yoshikoshi
etc, J. Am. Chem. Soc., 1984, 106, 2149-2156
OSi(CH3)3 NO2
R
O
O
R
+ Lewis acidO
R
SiMe2HDTBP
145°CSiMe2 SiMe2 SiMe2
SiMe2
Base-Induced Rearrangement of 1-(Trimethylsilyl)allyic Alcohols.
Stereo- and Regioselective Synthesis of Silyl Enol Ethers through
Lithium HomoenolatesIsao Kuwajima etc, J. Am. Chem. Soc., 1984,
106,1773-1778
R1
R2
R3
OLi
SiMe3
R1
R2
R3
OTMS
Li
R1
R2
R3
OTMS Li
R1
R2
R3
OTMS R4
R1
R2
R3
OLI TMS
alkylation
E. J. Corey:
A New Method for the synthesis of Organic Nitro CompoundsE. J.
Corey, Bertil Samuelsson and Fredrick A. LuzzioJ. Am. Chem. Soc.,
1984, 106, 3682-3683
R N3 R$3P+ RN PR3O3 RN PR3
OO
ORNO2 + R3P O
New and General Synthesis of Polycyclic "-Lactone by Double
AnnulationE. J. Corey and Myung-chol KangJ. Am. Chem. Soc., 1984,
106, 5384-5385
OH
O O
Mn3O(OAc)7CH3COOH
O
O O
Rhodium(I)-Catalyzed Hydrogenation of Olefin. The Documentation
of Hydroxyl-Directed Stereochemical Control in Cyclic and Acyclic
SystemsDavid A. Evans and Michael M. MorrisseyJ. Am. Chem. Soc.,
1984, 106, 3866-3868
OH
Rh(I)
OH
H2
Application: ACIEE, 2007, 46(4), 541-544
D. A. Evans:
Asymmetric Acylation Reactions of Chiral Imide Enolates. The
First Direct Approach to the Construction of Chiral !-Dicarbonyl
SynthonsD. A. Evans, M. D. Ennis and T. Le, J. Am. Chem. Soc.,
1984, 106, 3866-3868
NO
O O
R1
R2COCl NO
O O
R1
R2
O
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JACS: 1984 Year in Review
10
Jun ShiBaran Group Meeting3/28/2007
Palladium-catalyzed coupling of vinyl triflates with
organostannanes. A short synthesis of pleraplysillin-1William J.
Scott, G. T. Crisp, J. K. StilleJ. Am. Chem. Soc.; 1984; 106,
4630-4632.
Palladium-catalyzed cross-coupling of vinyl iodides with
organostannanes: synthesis of unsymmetrical divinyl ketonesW. F.
Goure, Michael E. Wright, P. D. Davis, Sharada S. Labadie, J. K.
StilleJ. Am. Chem. Soc.; 1984; 106; 6417-6422.
Palladium-catalyzed cross coupling of allyl halides with
organotin reagents: a method of joining highly functionalized
partners regioselectively and stereospecificallyForrest K. Sheffy,
J. P. Godschalx, J. K. StilleJ. Am. Chem. Soc.; 1984; 106;
4833-4840.
Palladium-catalyzed carbonylative coupling of vinyl triflates
with organostannanes.
A total synthesis of (±)-!9(12)-capnellene
G. T. Crisp, William J. Scott, John K. Stille
J. Am. Chem. Soc.; 1984;106, 7500-7506
J. K. Stille:
MeMe
Me
OTf
Me3SnTMS
Pd(PPh3)4/CO/LiCl1.
2. BF3•Et2O, 100°C
O
Me
MeMe
Me
MeMe
Capnellene
Asymmetric synthesis of quaternary carbon centersA. I. Meyers,
Michael Harre, Robert GarlandJ. Am. Chem. Soc.; 1984; 106;
1146-1148.
Asymmetric addition to chiral naphthyloxazolines. A facile route
to 1,1,2-trisubstituted 1,2-dihydronaphthalenes in high
enantiomeric excessBruce A. Barner, A. I. MeyersJ. Am. Chem. Soc.;
1984; 106; 1865-1866.
A. I. Meyers:
NO
Ph OMe
1. RLi2. E+
OX
R
H
E CHO
R
H
E
Ph COOH
O
H2N OH
+N
O
O
H
Ph
N
O
O
H
Ph
R1
LDA
R1X
Ph COOH
O R1
LDAR2X
N
O
O
R1
Ph
R2
H+
H+
Ph COOH
OR2 R1
B. M. Trost:
Sulfones as chemical chameleons. Cyclization via 1,1-dipole
synthonsBarry M. Trost, M. Reza ChadiriJ. Am. Chem. Soc.; 1984;
106, 7260-7261.
R1
C HPhSO2
R2
R1
C
R2
O
BrSO2Ph
OO
SO2Ph+
-
JACS: 1984 Year in Review
11
Jun ShiBaran Group Meeting3/28/20072-Alkoxybenzo-1,3-dithiole
1,1,3,3-tetraoxide. A carbonyl 1,1-dipole synthonBarry M. Trost,
Peter QuayleJ. Am. Chem. Soc.; 1984; 106, 2469-2471.
C
OO
TMS
SO2RRO2S
O
O2S SO2n TMS
TiCl4
n
O
Stereocontrolled 1,1,2-trialkylation of ketonesBarry M. Trost,
Alberto BrandiJ. Am. Chem. Soc.; 1984; 106, 5041-5043
OTMS R+
O
R
Hydroboration. 68. Chiral synthesis via organoboranes. 1. A
simple procedure to achieve products of essentially 100% optical
purity in hydroboration of alkenes with monoisopinocampheylborane.
Synthesis of boronic esters and derived products of very high
enantiomeric puritiesHerbert C. Brown, Bakthan SingaramJ. Am. Chem.
Soc.; 1984; 106, 1797-1800
Herbert C. Brown
BH3Li+H
MeI, 0°C HBH
Ipc
MiscellaneousDichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II):
an effective catalyst for cross-coupling of secondary and primary
alkyl Grignard and alkylzinc reagents with organic halidesTamio
Hayashi, Mitsuo Konishi, Yuji Kobori, Makoto Kumada, Taiichi
Higuchi, Ken HirotsuJ. Am. Chem. Soc.; 1984; 106, 158-163
MgCl R Br[ML2]
R3
R: a=Ph b=PhCHCH- c=PMB
Sulfoximine-directed osmylation: synthesis of enantiomerically
pure dihydroxycycloalkanonesCarl R. Johnson, Michael R. Barbachyn
J. Am. Chem. Soc.; 1984; 106; 2459-2461.
HO
PhS
O
NMe
HO
PhS
O
NMe HO OH
O
OH OH
SPh
O
NHMeSPh
O
NMe
O
Ring expansion and cleavage of succinoin derivatives. Geminal
acylation, reductive succinoylation, and stereoselective spiro
annelation methodsJunichi Shimada, Koichi Hashimoto, Byeang Hyean
Kim, Eiichi Nakamura, Isao Kuwajima J. Am. Chem. Soc.; 1984; 106,
1759-1773.
CO2Et
CO2EtOTMS
OTMS
R1R2
OO
O
R1
R2
