An Oxy-Cope Route to the Taxane AB Ring System

Abstract
The bridged taxane AB ring system is constucted via an oxy-Cope reaction of 6-hydroxy-7,7-dimethyl-1,6-divinylbicyclo-[3.1.1]heptane. The outcome of the intramolecular ketene-olefin cycloaddition of 2-ethylidene-7-methyl-6-octenoyl chloride used to construct the required oxy-Cope substrate is shown to be highly sensitive to 3-methyl substitution on the chain connecting the ketene and olefin.

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