Synthesis 2001(11): 1737-1741
DOI: 10.1055/s-2001-16748
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

A Formal Catalytic Asymmetric Synthesis of (+)-Biotin with Modified Cinchona Alkaloids

Chulho Choi, Shi-Kai Tian, Li Deng*
Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA
Fax: +1(781)7362516; e-Mail: deng@brandeis.edu;
Further Information

Publication History

Received 14 June 2001
Publication Date:
28 September 2004 (online)

Abstract

A formal catalytic asymmetric synthesis of (+)-biotin was realized. The key steps involve a catalytic, highly enantioselective and quantitative desymmetrization of a meso cyclic anhydride followed by a one-pot chemoselective reduction to form the optically active lactone intermediate in the Goldberg-Sternbach (+)-biotin synthesis.