Synthesis of racemic 2,4-dimethyltetradecanoic acid from Mycobacterium kansasii.
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.
Wallace
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PA
Department of Chemistry, University of Newcastle, Newcastle upon Tyne, UK.
Minnikin
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DE
D009161:Mycobacterium / Q000737:chemistry*; D009227:Myristic Acids / Q000138:chemical synthesis*; D013237:Stereoisomerism
C102748:2,4-dimethyltetradecanoic acid; D009227:Myristic Acids