Diastereoselective desulfurization of 5,6-dihydro-1,4-dithiins. Synthesis of muscalure from Musca domestica L.

Article abstract of DOI:10.1016/S0040-4020(01)85249-2

A procedure is reported for the chemo- and stereo-selective sulfur removal from 5,6-dihydro-1,4-dithiins which completes the pathway to synthesize cis configurated olefins from carbonyl compounds. A four step synthesis of (Z)- 9-tricosene (muscalure) with the dithiin moiety serving as the penultimate olefin precursor is also reported as an example of the proposed synthetic strategy.