Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates.
Tuberculostearic acid, (R)-10-methyloctadecanoic acid, is a characteristic component of pathogenic mycobacteria and related organisms. Sensitive detection of this acid in infected material allows rapid detection of mycobacterial disease. A novel, convergent synthesis of tuberculostearic acid and key chiral intermediates is described in this communication, to provide a reference compound. Racemic and (R)- and (S)-1-iodo-2-methyldecanes were synthesised from 1-octanal and 1-carboethoxyethylidenetriphenylphosphorane as initial starting materials. 1-Hydroxyoct-7-yne was made from 1,6-hexanediol by two alternative methods and coupled with the above racemic iodide. Hydrogenation and oxidation of the resulting (R,S)-10-methyloctadec-7-yn-1-ol gave racemic tuberculostearic acid.
Wallace
P A
PA
Department of Chemistry, University of Newcastle, Newcastle upon Tyne, UK.
Minnikin
D E
DE
McCrudden
K
K
Pizzarello
A
A
D010084:Oxidation-Reduction; D012997:Solvents; D013229:Stearic Acids / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012997:Solvents; D013229:Stearic Acids; C026082:tuberculostearic acid