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Diastereoselective synthesis of trans-fused tetrahydropyran derivatives of 5H-dibenzo[a,d]cycloheptene

✍ Scribed by Hua Mao; Mohamed Koukni; Tomasz Kozlecki; Frans Compernolle; Georges J. Hoornaert

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 245 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02111-1

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✦ Synopsis

The epoxides derived from 5H-dibenzo [a,d]cycloheptene and its 2-fluoro derivative were converted into the trans-fused hydropyran-3-one compounds (4aR*,13bS*)-(12-fluoro-)4,4a,9,13b-tetrahydrodibenzo [3,4:6,7]cyclohepta[1,2-b]pyran-3(2H)-one and the corresponding 3-amino derivative via two separate sequences. These involved opening of the epoxide by either a propargyl or allylmagnesium reagent followed by tungsten-mediated cyclisation of the alkynol or OsO 4 -catalysed transformation into the diol.

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