Mukapolide

Selective reduction of allyl sulfides implies that no scrambling of the carbon-carbon double bond occurs during the process. Effectively this has proved to be the case especially when lithium in ethylamine is used, and the method has allowed the regio- and stereo-selective synthesis of a large variety of 1,5-dienes including squalene (Scheme 25, entry a), mukapolide (Scheme 25, entry b), dendrolasin (Scheme 25, entry c), the basic nucleus of crassin acetate (Scheme 25, entry d) from 7,7-dialkylallyl sulfides and allyl halides, and also of 1,5-enynes " from propargyl sulfides and allyl halides (Scheme 34, entry b). 

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