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

✍ Scribed by Paul A. Wallace; David E. Minnikin

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 391 KB
• Volume: 82
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(96)02570-4

✦ Synopsis

A known intermediate, (3 R, S; 5 R,S)-3,5-dimethyl-6-triphenylmethyloxyhexanal gave. in a Wittig reaction with l-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.