Nm. Carballeira et M. Pagan, Total synthesis of the novel bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid, CHEM PHYS L, 113(1-2), 2001, pp. 23-27
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.