Session: Asymmetric Reactions & Syntheses:

By way of a one-pot Robinson annulation-epoxidation sequence catalyzed by benzyltrimethylammonium hydroxide (Triton B), the (+)-octalone derivative, epoxydecalinone-1, has been synthesized under mild reaction conditions in moderate yield. 2-Methylcyclohexanone and ethyl vinyl ketone were reacted under inert atmosphere at room temperature to obtain (+)-octalone. Simple computational studies indicate this intermediate is thermodynamically favored, but to further understand this stereoselectivity, mechanistic studies are ongoing. Tert-butyl hydroperoxide was then added to accomplish the sequential stereoselective epoxidation. The structure and absolute configuration of epoxydecalinone-1 were verified by X-ray crystallography.

Peter Smith

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