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

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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 (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).