The reaction of hyperforin with hydride reducing agents.

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

Research output: Contribution to journalArticlepeer-review

5 Citations (SciVal)

Abstract

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.
Original languageEnglish
Pages (from-to)5479-5484
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusPublished - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

  • acylphloroglucinols
  • natural products
  • reduction

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