Tetrahedron: Asymmetry

An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine

SK Taylor, M Ivanovic, LJ Simons, MM Davis

Index: Taylor, Stephen K.; Ivanovic, Milica; Simons, Lloyd J.; Davis, Matthew M. Tetrahedron Asymmetry, 2003 , vol. 14, # 6 p. 743 - 747

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Citation Number: 15

Abstract

Efficient, formal syntheses of aphanorphine and eptazocine are reported that involve epoxide cyclizations. The necessary chiral epoxides were prepared following treatment of diols prepared by Sharpless asymmetric osmylations of an alkene. The cyclizations formed a ring compound with the same enantiomeric purity as the starting epoxide.