Download PDF
Synthesis 1997; 1997(10): 1195-1198
DOI: 10.1055/s-1997-1334
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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