Synthesis 2006(23): 4005-4012  
DOI: 10.1055/s-2006-950331
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of (+)-Sedamine and (-)-Allosedamine

J. S. Yadav*, M. Sridhar Reddy, P. Purushothama Rao, A. R. Prasad
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 7 July 2006
Publication Date:
20 October 2006 (online)

Abstract

Two different approaches to the enantioselective syntheses of (+)-sedamine and (-)-allosedamine are described, both using the Sharpless asymmetric epoxidation as the key step. Regioselective reduction of epoxides, chemoselective oxidation of alcohols, ring-closing metathesis, and nucleophilic displacements were the other key steps employed.