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Paper | Special issue | Vol 52, No. 1, 2000, pp.261-272
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S20
Application of Oxidative Desymmetrization of meso-Tetrahydrofurans: Syntheses of Functionalized Chiral Building Blocks and of (-)-Alloyohimbane

Akio Miyafuji, Katsuji Ito, and Tsutomu Katsuki*

*Department of Molecular Chemistry, Graduate School of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

Oxidative desymmetrization of oxygen functionalized meso-tetrahydrofurans was successfully achieved (up to 87% ee) through (salen)manganese(III) catalyzed enantiotopic selective C-H oxidation. The enantioselective synthesis of (-)-alloyohimbane (12) has also been achieved in a short step by using oxidative desymmetrization of meso-tetrahydrofuran as the key step.