Tetrahedron

An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

H Wilhelm, LA Wessjohann

Index: Wilhelm, Heike; Wessjohann, Ludger A. Tetrahedron, 2006 , vol. 62, # 29 p. 6961 - 6966

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Citation Number: 25

Abstract

8-Prenylnaringenin, a flavonoid, is the strongest known phytoestrogen (plant derived estrogen mimic) used in phytomedicinal applications. Starting from xanthohumol a byproduct of hops-extraction, 8-prenylnaringenin can be synthesized via isoxanthohumol. Of various demethylation procedures tested, the best yield (92%) is obtained by treatment with scandium trifluoromethanesulfonate and potassium iodide without any need of protection. ...