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An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement

2001; Elsevier BV; Volume: 57; Issue: 6 Linguagem: Inglês

10.1016/s0040-4020(00)01078-4

1464-5416

Sven Gester, Peter Metz, Oliver Zierau, Günter Vollmer,

Allelopathy and phytotoxic interactions

Starting from commercially available naringenin (3), the flavanoids 8-prenylnaringenin (1) and 6-(1,1-dimethylallyl)naringenin (2) have been prepared in racemic form using prenyl ether 5 as a general intermediate. While a domino Claisen–Cope rearrangement of 5 was the key step in the synthesis of 1, the cytotoxic compound 2 was additionally secured via a europium(III)-catalyzed Claisen rearrangement of 5 at low temperature. Both 1 and 2 display strong estrogenic activities.