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Synthesis 1997; 1997(10): 1195-1198
DOI: 10.1055/s-1997-1334
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Total Synthesis of the Antimicrobial Fatty Acid (5Z,9Z)-14-Methylpentadeca-5,9-dienoic Acid and its Longer-Chain Analog (5Z,9Z)-24-Methylpentacosa-5,9-dienoic Acid

Elba D. Reyes, Néstor M. Carballeira*
  • *Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan, Puerto Rico 00931-3346, USA, Fax +1(787)751-0625; E-mail: ncarball@upracd.upr.clu.edu
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Publication Date:
31 December 2000 (online)

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The antimicrobial marine fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid, recently identified in the phospholipids of the Caribbean gorgonian Eunicea succinea, and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid, initially identified in the phospholipids of the sponge Petrosia ficiformis, have been synthesized for the first time through a common synthetic route. A combination of alkyne-bromide coupling and Wittig reaction resulted in the best combination for assembling the Δ 5,9 functionality in high yield and stereoselectivity.

(5Z,9Z)-14-methylpentadeca-5,9-dienoic acid - (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid - cytotoxic - fatty acids