Abstract

The epoxides derived from 5 H-dibenzo[ a, d]cycloheptene and its 2-fluoro derivative were converted to trans-fused hydrofurans 4a, b (55 and 44% overall yields) via a five-step sequence, i.e. (i) epoxide ring opening using propargylmagnesium bromide, (ii) mercury(II)-induced cyclisation and in situ bromination to give the bromomethylene substituted hydrofurans, (iii, iv) acid catalysed hydration and stereoselective reduction of the hemiacetal intermediates, and (v) base promoted cyclisation.

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