Stereocontrolled Total Synthesis of Lipoxins As and B₅

Abstract

Icosapentaenoic acids and their metabolites are of both nutritional and bio-medical interest. The title compounds were previously accessible in only very small amounts via biosynthetic routes. Their first total synthesis has now been achieved in good yield and in a stereocontrolled fashion. The key steps were a Pd0–Cu1-catalyzed coupling of terminal alkynes with vinyl halides to give the icosanoid skeleton and Lindlar hydrogenation to give the Z olefins.