Journal of Organic Chemistry p. 3819 - 3824 (1984)
Update date:2022-08-02
Topics:
Okazaki, Renji
Negishi, Yoshio
Inamoto, Naoki
The reaction of 1-mono- and 1,2-disubstituted 3,3-bis(methylthio)-2-propen-1-ones 1 with dimethylsulfonium methylide (2) affords 2,2-bis(methylthio)-2,5-dihydrofurans 3 via epoxide 8 which can be isolated in a special case.A couple of methods including acid treatment effected the conversion of 3 to 2-(methylthio)furans 4, which are found to be useful synthons of a variety of furans and butenolides.Two naturally occurring furans, perillene and rosefuran, were synthesized by this method.
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