ORGN 519 |
The first total synthesis of the bacterial 14-methyl-9(Z)-pentadecenoic acid, a potential bioactive fatty acid
| David J. Sanabria-Ríos, Lizabeth Giménez, Clarisa Cruz, and Néstor M. Carballeira. Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, P.O. Box 23346, San Juan, PR 00931-3346 |
| Several iso-branched fatty acids have shown interesting biological activity. For example, (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid, first isolated from Eunicea succinea was particularly active against Gram-positive bacteria such as Staphylococcus aureus and Streptococcus faecalis. On the other hand, the 14-methylpentadecanoic acid displays cytotoxicity against HeLa S3 cells possibly via topoisomerase I inhibition. In order to further study the bioactivity of this interesting class of methyl-branched fatty acids we have undertaken the total synthesis of the bacterial 14-methyl-9(Z)-pentadecenoic acid (1). Acid 1 was identified, for the first time, in sedimentary marine bacteria from mangrove stand on the Low Isles, North Queensland, Australia. Surprisingly and to the best of our knowledge, no previous synthesis for this acid has been reported. Therefore our synthesis of 1 started with commercially available 4-methyl-1-bromopentane and was achieved in 7 steps in an overall 4 % yield. Also, the synthesis of 14-methyl-5(Z)-pentadecenoic acid (2), the delta 5 analog of 1, was undertaken in order to study its bioactivity. The details of these syntheses will be presented. 
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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