Absolute Configuration and Synthesis of (+)-Caudoxirene, the Gamete-Releasing and Gamete-Attracting Pheromone of the Brown Alga Perithalia caudata (Phaeophyceae)

Article abstract of DOI:10.1002/hlca.19920750311

The absolute configuration of the gamete-releasing and -attracting pheromone 2-vinyl-3-(5'-vinylcyclopent-2'-enyl)oxirane ( = (+)-caudoxirene; (+)-1) of the marine brown alga Perithalia caudata is established as (2R,3R,1'S,5'S).Highly diastereoselective syntheses and the biological activities of three diastereoisomers of 1 are described.Compound (+)-(2R,3R,1'S,5'S)-1 is the first fully characterized epoxypheromone from marine brown algae (Phaeophyceae).