Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates

Article abstract of DOI:10.1016/0009-3084(94)90067-1

Tuberculostearic acid (R)-10-methyloctadecanoic acid, is a characteristic component of pathogenic mycobacteria and related organisms.Sensitive detection of this acid 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. Keywords: Mycobacterium tuberculosis; Tuberculostearic acid; Acetylene coupling; (R,S)-10-methyloctadecanoic acid; Chiral 2-methyl branched fatty acids