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Oxidative Fragmentation of the Bridged β-Triketone Core of Hyperforin

✍ Scribed by Luisella Verotta; Erminio Lovaglio; Olov Sterner; Giovanni Appendino; Ezio Bombardelli

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 105 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300568

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✦ Synopsis

Abstract

The β‐triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide‐induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C‐1 carbonyl bridge. A mechanistic rationale for this process is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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