| Abstract: | The title compound 2 was readily prepared by MCPBA oxidation of the sulfide 1. Thermal desulfonylation of 2 gave the sulfoxide‐substituted diene 3. The Diels‐Alder reactions of 3 with various dienophiles gave the cyclized products 4‐9 in good yields. The regiochemistry was found to be dominated by the phenylsulfinyl group, but could be reversed by the presence of a Lewis acid. Deprotonation of 2 by BuLi, followed by the reaction with alkyl halides, gave the substituted 2‐sulfolenes 10. A synthetic application of 10 was demonstrated by converting 10e to the bicyclic product 11. |
