Resolution of (±)– Cytallene — A Highly Active Anti-HIV Agent with Axial Dissymmetry

Bryan Colin Nicholas Morgan Jones Department of Chemistry, Michigan Cancer Foundation

Claire Simons Department of Chemistry, Michigan Cancer Foundation

Hisao Nishimura Chiral Technologies, Inc., Exton, Pennsylvania, 19341, U.S.A.

Jiri Zemlicka Department of Chemistry, Michigan Cancer Foundation; Departments of Internal Medicine and Biochemistry, Wayne State University School of Medicine, Detroit, Michigan, 48201, U.S.A.

Abstract

Anti-HIV agent (±)-cytallene (1b + 2b) was resolved by enantioselective acylation of (±)-N⁴-benzoylcytallene (1d + 2d) with vinyl butyrate in tetrahydrofuran catalyzed by lipase AK from Pseudomonas sp. and subsequent deacylation of 4d and 1d with ammonia in methanol. Optically pure enantiomers 1b and 2b were obtained.

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Resolution of (±)– Cytallene — A Highly Active Anti-HIV Agent with Axial Dissymmetry

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Resolution of (±)– Cytallene — A Highly Active Anti-HIV Agent with Axial Dissymmetry

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