SYNTHESIS OF (2R 4R,S)-DIMETHLYDOCOSANOIC AND (2S 4R,S)-DIMETHYLDOCOSANOIC ACIDS

被引：6

作者：

WALLACE, PA ^{[1
]}

MINNIKIN, DE ^{[1
]}

机构：

[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1994年 / 72卷 / 01期

关键词：

(2R; 4R; S)-; AND; (2S; S)-DIMETHYLDOCOSANOIC ACID; MYCOSANOIC ACID; MYCOBACTERIUM TUBERCULOSIS; 2,3-DI-O-ACYL-ALPHA,ALPHA-TREHALOSE; (R)-(-)-NAPHTHYLETHYLAMIDES;

D O I：

10.1016/0009-3084(94)90019-1

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

2,4-Dimethyldocosanoic acid is a major acyl component of 2,3-di-O-acyl-alpha,alpha-trehalose glycolipid antigens isolated from Mycobacterium tuberculosis. Racemic 2,4-dimethyldocosanoic acid has been synthesized and the chiral centre at C-2 resolved as an (R)-(-)-naphthylethylamide. An isomeric mixture of 3,5-dimethylcyclohexan-1-ols was oxidised to isomeric 3,5-dimethylcyclohexan-1-ones. This was subjected to Baeyer-Villiger oxidation to give isomeric 3,5-dimethylcaprolactones. Ring opening under alkaline conditions followed by phase-transfer catalysed esterification gave isomeric methyl 3,5-dimethyl-6-hydroxyhexanoates. Protection of the alcohol with triphenylmethyl chloride followed by lithium aluminium hydride reduction and pyridinium chlorochromate oxidation gave isomeric 3,5-dimethyl-6-triphenylmethyloxyhexanals. Coupling with hexadecyltriphenylphosphonium bromide, followed by trityl deprotection and hydrogenation of the remaining alkene, yielded isomeric 2,4-dimethyldocosanoic acids, which were resolved at C-2 as diastereoisomeric (R)-(-)-naphthylethylamides.

引用

页码：87 / 101

页数：15

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