Synlett

A new method to prepare 3-Alkyl-2-hydroxy-1, 4-naphthoquinones: synthesis of lapachol and phthiocol

SB Ferreira, DR da Rocha, JWM Carneiro, WC Santos

Index: Ferreira, Sabrina Baptista; Rodriguesdarocha, David; Carneiro, Jose Walkimar M.; Santos, Wilson Costa; Ferreira, Vitor Francisco Synlett, 2011 , # 11 p. 1551 - 1554

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Citation Number: 13

Abstract

Abstract In this article a mild, simple, safe, and chemoselective synthesis and reduction of o- quinone methides to the corresponding 3-alkyl-2-hydroxy-1, 4-naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural ...