Oxidative fragmentation of the bridged beta-triketone core of hyperforin
The beta-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).