Preparation and Reactions of a 7,8-Epoxymorphinan: Formation of a 7,8-Unsaturated Morphinan and Unprecedented Conversion to Cyclobutylcarbinol Derivatives

Abstract
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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