Tetrahedron letters

Regioselective synthesis of 3-aryl-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids as potential insulin receptor activators

SY Chou, SST Chen, CH Chen, LS Chang

Index: Chou, Shan-Yen; Chen, Shieh-Shung Tom; Chen, Ching-Hui; Chang, Lien-Shange Tetrahedron Letters, 2006 , vol. 47, # 43 p. 7579 - 7582

Full Text: HTML

Citation Number: 7

Abstract

3-Methoxy-4-aryl-furan-2, 5-dicarboxylic acid (8) is selectively converted into its C-5 methylester (6) by treatment with methyl chloroformate followed by decarboxylation in one flask. Acylation of the resulting half ester with a 7-substituted indole was performed under mild conditions to afford 3-aryl-5-(1H-indole-3-carbonyl)-4-methoxy-2-furoic acid (11). The synthetic utility of the resulting furoic acids as a skeleton in the synthesis of potential ...