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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1363-1373
Published online, 26th September, 2011
DOI: 10.3987/COM-11-S(P)87
Diastereoselective Synthesis of (±)-Deethyleburnamonine Using a Catalytic Cyclopropane Ring-Opening / Friedel-Crafts Alkylation Strategy

Dadasaheb V. Patil, Marchello A. Cavitt, and Stefan France*

*School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332-0400, U.S.A.

Abstract

A short, diastereoselective synthesis of (±)-deethyleburnamonine is reported with an overall yield of ~18% over six steps. The key synthetic step involves an indium(III)-catalyzed tandem ring-opening/Friedel-Crafts alkylation of a donor-acceptor-acceptor amino cyclopropane to generate the ABDE portion of the target.