Total synthesis of the novel bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid

The recently discovered bacterial fatty acid 16-methyl-8(Z)-heptadecenoic a cid was synthesized for the first time in four steps (22%, overall yield) s tarting from commercially available 8-methylnonanoic acid. The synthetic ap proach provided enough material to corroborate the structure and stereochem istry of the acid, which was recently identified in a Micrococcus bacterium from Lake Pomorie in Bulgaria. Reference equivalent-chain length values in nonpolar capillary gas chromatography for methyl 16-methyl-8(Z)-heptadecen oate and methyl 16-methyl-8(E)-heptadecenoate are also reported. This infor mation will be helpful in subsequent characterizations of these fatty acids . as well as in the total identification of the fatty acid profile of bacte ria producing these compounds. (C) 2001 Elsevier Science Ireland Ltd. All r ights reserved.