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Planta Med 1985; 51(6): 501-504
DOI: 10.1055/s-2007-969575
Research Articles

© Georg Thieme Verlag Stuttgart · New York

Cycloetherification of Hydroxyoleanenes by N-Bromosuccinimide

Won Sick Woo1 , Sam Sik Kang1 , Sang-sup Jew2
  • 1Natural Products Research Institute, Seoul National University, Seoul 110, Korea
  • 2College of Pharmácy, Seoul National University, Seoul 151, Korea
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Publication History

1985

1985

Publication Date:
26 February 2007 (online)

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Abstract

Treatment of 28-hydroxyolean-12-enes with N-bromosuccinimide (NBS) in acetonitrile at room temperature afforded 12 α-bromooleanan-13β, 28-epoxides in high yield. This reaction resulted in the formation of olean-9 (11), 12-diene-18α, 29-epoxides from 29-hydroxy isomers but recovered only starting materials from 30-hydroxy isomers. NBS will be used a reagent for diagnostic tool to distinguish between isomers bearing a primary hydroxyl group on D/E rings of olean-12-enes.

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