Enantioselective synthesis of γ-lactones from thioglycolic acid:: Syntheses of (-)-muricatacin and 5-epi-(-)-muricatacin

被引：23

作者：

Chang, SW ^{[1
]}

Hung, CY ^{[1
]}

Liu, HH ^{[1
]}

Uang, BJ ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(98)00007-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An approach for the enantioselective synthesis of functionalized gamma-lactones and its application to the syntheses of (-)-muricatacin 1a and 5-epi-(-)-muricatacin 1b is reported. A sequential oxidation of the intermediate 4 with m-chloroperoxybenzoic acid was conducted to realize the reaction mechanism. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：521 / 529

页数：9

共 22 条

[1] Burkert U., 1982, Molecular Mechanics
[2] CHANG YL, 1993, THESIS NATL TSING HU
[3] STEREOSPECIFIC SYNTHESIS OF (+)-MURICATACIN - A BIOLOGICALLY-ACTIVE ACETOGENIN DERIVATIVE
FIGADERE, B
HARMANGE, JC
LAURENS, A
CAVE, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (51) : 7539 - 7542
[4] SYNTHESIS OF (-)-MURICATACIN AND (-)-(5R,6S)-6-ACETOXY-5-HEXADECANOLIDE, THE MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE, FROM D-ISOASCORBIC ACID
GRAVIERPELLETIER, C
SANIERE, M
CHARVET, I
LEMERRER, Y
DEPEZAY, JC
[J]. TETRAHEDRON LETTERS, 1994, 35 (01) : 115 - 118
[5] SULFOXIDE-MEDIATED INTRAMOLECULAR HYDROXYLATION OF A REMOTE OLEFIN IN AN ACYCLIC SYSTEM
HAUSER, FM
ELLENBERGER, SR
CLARDY, JC
BASS, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (08) : 2458 - 2459
[6] SYNTHESIS OF (4R,5S)-(-)-L-FACTOR AND (4S,5S)-(+)-L-FACTOR AND MURICATACIN FROM D-GLUCOSE
KANG, SK
CHO, HS
SIM, HS
KIM, BK
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (06) : 807 - 812
[7] LIU HH, 1990, TETRAHEDRON LETT, V31, P257
[8] LIU ZY, 1993, CHINESE CHEM LETT, V4, P663
[9] LOFSTROM CMG, 1995, J ORG CHEM, V60, P3586
[10] Total synthesis of (+)-4-deoxygigantecin
Makabe, H
Tanaka, A
Oritani, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (24) : 4247 - 4250

← 1 2 3 →