Absolute Configuration and Synthesis of (+)‐Caudoxirene, the Gamete‐Releasing and Gamete‐Attracting Pheromone of the Brown Alga <i>Perithalia caudata</i> (Phaeophyceae)

Abstract

Abstract 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 (2 R ,3 R ,1′ S ,5′ S ). Highly diastereoselective syntheses and the biological activities of three diastereoisomers of 1 are described. Compound (+)‐(2 R ,3 R ,1′ S ,5′ S )‐ 1 is the first fully characterized epoxypheromone from marine brown algae (Phaeophyceae).