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The reaction of hyperforin with hydride reducing agents.

På svenska

Author

  • Luisella Verotta
  • Olov Sterner
  • Giovanni Appendino
  • Ezio Bombardelli
  • Tullio Pilati

Summary, in English

As part of a study aimed at generating analogues of hyperforin (1), the reaction of this prenylated phloroglucinol with various hydride reducing agents was investigated. Hyperforin contains two beta-dicarbonyl systems, one of which is non-enolizable, and it was interesting to assess the relative reactivity of these structural elements in the highly compact framework of the natural product. Depending on the reducing agent employed, a surprising range of compounds could be obtained, sometimes in synthetically useful yields. The stereochemistry of the LiAlH4-reduced product was secured by X-ray analysis and served as a base for elucidating the configuration of a series of reduced and deoxygenated analogues obtained with other reducing agents. The chemoselectivity observed in these reactions is apparently the result of a combination of metal-chelation and hydrogen-bonding effects.

Publishing year

2006

Language

English

Pages

5479-5484

Publication/Series

European Journal of Organic Chemistry

Document type

Journal article

Publisher

John Wiley & Sons Inc.

Topic

  • Organic Chemistry

Keywords

  • acylphloroglucinols
  • natural products
  • reduction

Status

Published

ISBN/ISSN/Other

  • ISSN: 1434-193X