A General and Stereospecific Synthesis of Cis Alkenes via Stepwise Hydroboration: A Simple Synthesis of Muscalure, the Sex Pheromone of the Housefly (Musca domestica)
A General and Stereospecific Synthesis of Cis Alkenes via Stepwise Hydroboration: A Simple Synthesis of Muscalure, the Sex Pheromone of the Housefly (Musca domestica)
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Date
1982-01-01
Authors
Brown, Herbert C.
Basavaiah, D.
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Abstract
Base-induced iodination of the vinylborane intermediates, conveniently obtained via the hydroboration of 1-alkynes with alkylbromoboranes (RBHBr·SMe2), provides cis-disubstituted alkenes in good yields. Muscalure, the insect pheromone of the housefly (Musca domestica), has been prepared in 59% yield. © 1982, American Chemical Society. All rights reserved.
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Journal of Organic Chemistry. v.47(19)