Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis

✍ Scribed by S. Hartmann; D.E. Minnikin; H.-J. Römming; M.S. Baird; C. Ratledge; P.R. Wheeler

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 712 KB
• Volume: 71
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(94)02315-8

✦ Synopsis

Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropcn-l-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-l-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-l-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (Z)-4-(2-octadecylcyclopropan-l-yi)butanoate and methyl (Z)-5-(2-octadecylcyclopropan-l-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-l-yl)propanoate involved protection of the cyclopropcne ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.