Helvetica Chimica Acta

Stereoselective Synthesis of cis??and trans??3, 4??Dihydro??3, 4, 8??trihydroxynaphthalen??1 (2H)??one

E Couché, A Fkyerat, R Tabacchi

Index: Couche, Emmanuel; Fkyerat, Abdellatif; Tabacchi, Raffaele Helvetica Chimica Acta, 2009 , vol. 92, # 5 p. 903 - 917

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Citation Number: 10

Abstract

A short and efficient protocol for the stereoselective synthesis of racemic trans-and cis-3, 4- dihydro-3, 4, 8-trihydroxynaphthalen-1 (2H)-one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (ž 5-hydroxynaphthalene-1, 4-dione; 12)(Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1, 2, 3, 4- ...