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Tandem reduction-chloroallylboration of esters: Asymmetric synthesis of lamoxirene, the spermatozoid releasing and attracting pheromone of the Laminariales (Phaeophyceae)

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Hertweck,  C.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Boland,  W.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Hertweck, C., & Boland, W. (2000). Tandem reduction-chloroallylboration of esters: Asymmetric synthesis of lamoxirene, the spermatozoid releasing and attracting pheromone of the Laminariales (Phaeophyceae). Journal of Organic Chemistry, 65(8), 2458-2463. doi:10.1021/jo991629r.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0012-A0B9-5
Abstract
The asymmetric synthesis of all four stereoisomers of lamoxirene (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane), the spermatozoid-releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Chiral ethyl cyclohepta-2,5-diene carbox