ORGN 582 |
| The fatty acids (Z)-13-methyltetradec-8-enoic acid (1) and the (Z)-15-methylhexadec-10-enoic acid (2) are bacterial fatty acids with a considerable biological potential. These methyl-branched fatty acids, with the unusual C-8 and C-10 unsaturations, are of interest as biomarkers for alkane-utilizing bacteria in soils and as biomarkers for sulphate-reducing bacteria such as Desulfovibrio sp., also found in wetland sediments. In addition, these bacterial fatty acids remain under-explored as possible therapeutic agents despite the fact that saturated iso-branched fatty acids with similar chain lengths have displayed considerable topoisomerase-I inhibition and also cytotoxicity. Therefore, as part of our program aimed at the total synthesis of unusual fatty acids with therapeutic potential we have accomplished the first total syntheses of 1 and 2 following a similar synthetic sequence consisting of seven steps and using (trimethylsilyl)acetylene as the key reagent in the synthesis. The overall yields for these syntheses ranged between 25% and 31%. The total syntheses of these fatty acids and their biological potential will be presented.
|
|
New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
