Concise Biomimetic Total Syntheses of Both Antipodes of Balasubramide

Michael B. Johansen; Andrew B. Leduc; Michael A. Kerr

doi:10.1055/s-2007-986670

LETTER

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;

Abstract

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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

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References

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