Synthesis of racemic 2,4-dimethyltetradecanoic acid from Mycobacterium kansasii.

Abstract:

:A known intermediate, (3 R, S; 5 R,S)-3,5-dimethyl-6-triphenylmethyloxyhexanal gave, in a Wittig reaction with 1-octyltriphenylphosphonium bromide and n-butyl lithium in anhydrous tetrahydrofuran, a mixture of olefininic compounds. Trityl deprotection and hydrogenation of the double bond afforded the (2 R, S; 4 R,S)-2,4-dimethyltetradecanols. Oxidation of the alcohol functionality using pyridinium dichromate in anhydrous N,N'-dimethylformamide gave racemic, (2 R, S; 4 R,S)-2,4-dimethyltetradecanoic acids, which were converted to their methyl esters. 2,4-Dimethyltetradecanoic acids are constituents of glycolipid antigens from Mycobacterium kansasii.

journal_name

Chem Phys Lipids

authors

Wallace PA,Minnikin DE

doi

10.1016/0009-3084(96)02570-4

subject

Has Abstract

pub_date

1996-08-19 00:00:00

pages

141-6

issue

2

eissn

0009-3084

issn

1873-2941

pii

0009308496025704

journal_volume

82

pub_type

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