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■ Syntheses of (—)-9-Demethylprotoemethinol and (±)- and (—)-10-demethylprotoemetinols

Tozo Fujii, Masashi Ohba, Hitoshi Suzuki, Satyesh C. Pakrashi, and Esahak Ali

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

The synthesis of (—)-9-demethylprotoemetinol (X) was achieved by LiAlH₄ reduction of the (—)-tricyclic ester XIV followed by catalytic hydrogenolysis of the resulting (—)-tricyclic alcohol XI. Acetylation of (—)-X yielded the (—)-diacetate XVII. Parallel synthetic routes starting with the isomeric (±)- and (—)-tricyclic esters XV gave (±)- and (—)-10-demethylprotoemetinols (XII) and the corresponding diacetates [(±)- and (—)-XVIII] through the (±)- and (—)-tricyclic alcohols XIII, respectively.