By way of a one-pot Robinson annulation-epoxidation sequence catalyzed by benzyltrimethylammonium hydroxide (Triton B), the (+)-octalone derivative, epoxydecalone 15, has been synthesized under mild reaction conditions. 2-Methylcyclohexanone 8 and ethyl vinyl ketone 7 were reacted under atmosphere at room temperature to obtain dimethyldecal-2-en-1-one 14. Literature reports indicate the cis-conformation of this intermediate is thermodynamically favored, but to further understand the stereoselectivity, mechanistic studies are ongoing.1,5,7 Tert-butyl hydroperoxide was then added to the (+)-octalone to accomplish the stereoselective epoxidation. The structure was verified via ATR-IR and NMR. In future studies, the absolute configuration of this product will be verified by X-ray crystallography and NOESY.

Asymmetric, one-pot Robinson annulation-epoxidation sequence

ACS Spring Meeting 2021

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