95. Structure and Synthesis of (+/-)-Caudoxirene, a New Spermatozoid-Releasing and -Attracting Pheromone from the Marine Brown Alga Perithalia caudata (Phaeophyceae, Sporochnales)

Article abstract of DOI:10.1002/hlca.19900730419

cis-3-(trans-1,2-Epoxybut-3-enyl)-4-vinylcyclopentene ((+/-)-4, caudoxirene) is a new gamete-releasing and gamete-attracting pheromone from the marine brown alga Perithalia caudata (Sporochnales).The key step of its synthesis is the diastereoselective alkylation of the aldehyde 8 with the <(phenylthio)allyl>titanium reagent 9 to yield the erythro-β-hydroxy sulfide 10 which affords 4 on sequential treatment with Me3O*BF4 and aq.NaOH.The lowest effective concentration of (+/-)-4 for gamete-release is found at 1.4 x 10^-11 mol/l seawater.