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- Title
Structure and Synthesis of (±)-Caudoxirene, a New Spermatozoid-Releasing and -Attracting Pheromone from the Marine Brown Alga Perithalia caudata (Phaeophyceae, Sporochnales). Part V.
- Authors
Wirth, Dieter; Boland, Wilhelm
- Abstract
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 × 10−11 mol/l seawater.
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 4, p916
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730419