ASYMMETRIC-SYNTHESIS OF GAMMA-HYDROXY ALPHA,BETA-UNSATURATED AMIDES VIA AN AD-ELIMINATION PROCESS - SYNTHESIS OF (+)-CORIOLIC ACID

被引：31

作者：

BENNANI, YL ^{[1
]}

SHARPLESS, KB ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 13期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)60351-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, asymmetric synthetic route to gamma-hydroxy alpha,beta-unsaturated ketone and/or aldehyde equivalents is described. Thus, 3,4-dihydroxy N-methoxy-N-methyl amides are treated in a one pot process with thionyl chloride followed by DBU to give the corresponding gamma-hydroxy alpha,beta-unsaturated amides in good yields. Based on this methodology, a short sequence leading to natural (+)-Coriolic acid is presented.

引用

页码：2083 / 2086

页数：4

共 37 条

[1] AMBERG W, IN PRESS J ORG CHEM
[2] ARAI M, 1992, SYNLETT, P309
[3] ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES
BENNANI, YL
SHARPLESS, KB
[J]. TETRAHEDRON LETTERS, 1993, 34 (13) : 2079 - 2082
[4] OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG
BURGESS, K
CASSIDY, J
HENDERSON, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2050 - 2058
[5] LIPASE-CATALYZED KINETIC RESOLUTION OF GAMMA-HYDROXY PHENYL SULFONES
CARRETERO, JC
DOMINGUEZ, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3867 - 3873
[6] CONVERGENT STEREOCONTROLLED SYNTHESIS OF 13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID (13-HODE)
CHAN, C
COX, PB
ROBERTS, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) : 971 - 972
[7] COREY EJ, 1989, LOGIC CHEM SYNTHESIS, P249
[8] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - THE EFFECT ON STEREOSELECTIVITY OF ALLYLIC SUBSTITUTION
CRAIG, D
READER, JC
[J]. TETRAHEDRON LETTERS, 1992, 33 (28) : 4073 - 4076
[9] SORBIC ACID IRON TRICARBONYL COMPLEX AS RESOLVING AGENT - CHIRAL SYNTHESES OF 4-HYDROXY NONENAL AND CORIOLIC ACID
DEMONTARBY, L
MOSSET, P
GREE, R
[J]. TETRAHEDRON LETTERS, 1988, 29 (32) : 3937 - 3940
[10] AN EFFICIENT PREPARATION OF OPTICALLY-ACTIVE (E)-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED PHENYL SULFONES USING LIPASE-MEDIATED ACYLATIONS
DOMINGUEZ, E
CARRETERO, JC
FERNANDEZMAYORALAS, A
CONDE, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (38) : 5159 - 5162

← 1 2 3 4 →