Tetrahedron letters

An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation

A Pezzella, L Lista, A Napolitano, M d'Ischia

Index: Pezzella, Alessandro; Lista, Liliana; Napolitano, Alessandra; D'Ischia, Marco Tetrahedron Letters, 2005 , vol. 46, # 20 p. 3541 - 3544

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Citation Number: 53

Abstract

A one-pot procedure for the preparation of catecholestrogens in over 90% yield is reported, involving oxygenation of 17β-estradiol or estrone with o-iodoxybenzoic acid (IBX) followed by reduction with methanolic NaBH4. The procedure, which was extended to the o- hydroxylation of a number of representative phenols in good-to-high yields, expands significantly the scope of phenolic oxidation mediated by IBX.