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The reaction of hyperforin with hydride reducing agents.

Author:
  • Luisella Verotta
  • Olov Sterner
  • Giovanni Appendino
  • Ezio Bombardelli
  • Tullio Pilati
Publishing year: 2006
Language: English
Pages: 5479-5484
Publication/Series: European Journal of Organic Chemistry
Document type: Journal article
Publisher: John Wiley & Sons

Abstract 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.

Keywords

  • Organic Chemistry
  • acylphloroglucinols
  • natural products
  • reduction

Other

Published
  • ISSN: 1434-193X
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

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