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Highly efficient synthesis of (±)-lamoxirene, the gamete-releasing and gamete-attracting pheromone of the Laminariales (Phaeophyta)

✍ Scribed by Christian Hertweck; Wilhelm Boland

Book ID: 104208121
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 283 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)01008-9

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✦ Synopsis

An efficient and highly diastereoselective synthesis of lamoxiren¢ (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane, 4), the gamete releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Ethyl cyclohepta-2,5-diene carbox~ylate ( ) is effectively alkylated to provide the svn-a-chlorohydrin 8 via reductive chloroallylboration with DIBAL-H and (Z)-y-chloroailyl-BBN. Cyclisation of the ehlorohydrin 8 is readily achieved with DBU yielding the pheromone in 25% overall yield from the cyclopropyl ester 5.

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