Regioselective lithiation and functionalization of 3-(benzyloxy) isothiazole: application to the synthesis of thioibotenic acid

…, P Krogsgaard-Larsen, U Madsen

Index: Bunch, Lennart; Krogsgaard-Larsen, Povl; Madsen, Ulf Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2375 - 2377

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Citation Number: 19

Abstract

Direct functionalization of the 3-oxygenated isothiazole heteroaromatic parental system has not yet been reported in the literature. Here, we report the first regioselective lithiation of the 5-position of 3-(benzyloxy) isothiazole (4) using LDA in diethyl ether. The versatility of the methodology was explored by quenching with a variety of electrophiles to give the desired products 7a, b, dg in 54-68% yield. Only benzoylation aiming at the synthesis of 7c was ...