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Stereoselective synthesis of trans-fused tetrahydrofuran derivatives of 5H-dibenzo[a,d]cycloheptene

✍ Scribed by Frans Compernolle; Hua Mao; Abdellah Tahri; Tomasz Kozlecki; Erik Van der Eycken; Bart Medaer; Georges J Hoornaert

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 123 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00404-5

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✦ Synopsis

The epoxides derived from 5H-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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