SYNTHESIS OF RACEMIC 2,4-DIMETHYLTETRADECANOIC ACID FROM MYCOBACTERIUM-KANSASII

A known intermediate, (3 R, S; 5 R,S)-3,5-dimethyl-6-triphenylmethylox yhexanal gave, in a Wittig reaction with 1-octyltriphenylphosphonium b romide and n-butyl lithium in anhydrous tetrahydrofuran, a mixture of olefininic compounds. Trityl deprotection and hydrogenation of the dou ble bond afforded the (2 R, S; 4 R,S)-2,4-dimethyltetradecanols. Oxida tion of the alcohol functionality using pyridinium dichromate in anhyd rous N,N'-dimethylformamide gave racemic, (2 R, S; 4 R,S)-2,4-dimethyl tetradecanoic acids, which were converted to their methyl esters. 2,4- Dimethyltetradecanoic acids are constituents of glycolipid antigens fr om Mycobacterium kansasii.