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Synlett 2007(16): 2593-2595  
DOI: 10.1055/s-2007-986670
LETTER
© Georg Thieme Verlag Stuttgart · New York

Concise Biomimetic Total Syntheses of Both Antipodes of Balasubramide

Michael B. Johansen, Andrew B. Leduc, Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada
Fax: +1(519)6613022; e-Mail: makerr@uwo.ca;
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Publication History

Received 8 June 2007
Publication Date:
12 September 2007 (online)

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Abstract

A two-step, protecting-group-free synthesis of the ­natural product balasubramide, using an Yb(OTf)3-catalyzed ­intramolecular epoxide opening, is reported. Both enantiomers of the natural product are available from the antipodal forms of the starting epoxycinnamic acid.

Key words

balasubramide - biomimetic synthesis - lanthanide ­catalysis - chiral resolution - indole natural product