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

Article abstract of DOI:10.1055/s-1997-1334

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.