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Synlett 1990; 1990(7): 384-386
DOI: 10.1055/s-1990-21098
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Preparation and Reactions of a 7,8-Epoxymorphinan: Formation of a 7,8-Unsaturated Morphinan and Unprecedented Conversion to Cyclobutylcarbinol Derivatives

Harry Finch* , Laurence M. Harwood, Roma Highcock, Brian Jackson, Keith Prout, Graeme Robertson, Richard C. Sewell
  • *Glaxo Group Research, Park Road, Ware SG12 0DJ, England
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Publication Date:
08 March 2002 (online)

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A radical cyclisation process has been applied to the epoxidised substrate 6, permitting access to a 7,8-unsaturated morphinan 11 after unmasking the double bond. In addition, reaction of the intermediate 7,8-epoxymorphinan 7 with Lewis acidic hydride reducing agents led to the unprecedented formation of products 13 and 14 incorporating the 7-oxatricyclo[3.2. 1.03,6]octane ring system containing the cyclobutylcarbinol moiety.

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