Abstract
The allylic sulphoxides 1b and 1e reacted with 1-pyrrolidinylcyclohexene and 2-ethoxycarbonyl cyclopentanone to yield the 2-substituted keto-sulphoxides 10 and 14 respectively, which on reduction followed by oxidation yielded in each case a mixture of cis and trans sulphones that were separated by column chromatography. Base induced cyclisation followed by reductive desulphurisation of the cyclised sulphones yielded the corresponding bicyclic compounds 6, 7, 8 and 9 in good yields. Alkylation products of 1 with cyclohexanone enamine and 2-methoxycarbonylcyclopentanone on reduction followed by oxidation yielded pairs of alkenyl sulphones that were separated and cyclised into 1-oxabicycles. [Display omitted]
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