Transition-metal-controlled synthesis of (.+-.)-aristeromycin and (.+-.)-2', 3'-diepi-aristeromycin. An unusual directive effect in hydroxylations

BM Trost, GH Kuo, T Benneche

Index: Trost; Kuo; Benneche Journal of the American Chemical Society, 1988 , vol. 110, # 2 p. 621 - 622

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Citation Number: 196

Abstract

The biological significance of carbocyclic analogues of nucleosides and of hydroxyalkylated purines' and the widespread use of protecting groups in the synthesis of such compounds led us to explore whether transition-metal-catalyzed alkylations would enhance selectivity and, consequently, improve synthetic efficiency. An initial question relates to regioselectivity as exemplified by the reaction of 2-pyrimidinone with vinyl epoxide 1 (eq 1). Unlike