The synthesis of both enantiomers of lactobacillic acid and mycolic acid analogues.

被引：18

作者：

Coxon, GD

Knobl, S

Roberts, E

Baird, MS

Al Dulayymi, JR

Besra, GS

Brennan, PJ

Minnikin, DE

机构：

[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

[3] Colorado State Univ, Dept Microbiol, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 36期

基金：

美国国家卫生研究院;

关键词：

asymmetric cyclopropanation; enzymatic desymmetrisation; chiral cyclopropanes; fatty acids; lactobacillic acid; mycolic acids; Simmons-Smith reaction;

D O I：

10.1016/S0040-4039(99)01378-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(11R, 12S)-lactobacillic acid (1) has been prepared either from D-mannitol by asymmetric cyclopropanation or from cycyclopropane-1, 2-dimethanol by enzymatic desymmetrisation. The syntheses of (11S, 12R)-lactobacillic acid (2) and (1R, 2S) 1(3'-methoxycarbonylpropyl)-2-octadecylcopropane (26) and related analogues (27 and 28) have also been achieved. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6689 / 6692

页数：4

共 21 条

[1]

BROTHERTON T, 1957, J AM CHEM SOC, V79, P5232

[2] AN UNEXPECTED REVERSAL OF FLUORINE SUBSTITUENT EFFECTS IN THE BIOMETHYLENATION OF 2 POSITIONAL ISOMERS - A SERENDIPITOUS DISCOVERY [J].