Synthetic studies toward diazonamide A. Preparation of the benzofuranone-indolyloxazole fragment

P Wipf, F Yokokawa

Index: Wipf, Peter; Yokokawa, Fumiaki Tetrahedron Letters, 1998 , vol. 39, # 16 p. 2223 - 2226

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Citation Number: 66

Abstract

The benzofuranone-indolyloxazole fragment of the polycyclic marine natural product diazonamide A was prepared from tryptamine. The oxazole ring was synthesized from an α keto-indole via cyclodehydration with Ph 3P Cl 3CCCl 3, and after selective Stille biaryl coupling with 2-iodo-6-stannylphenol, the benzofuranone ring was constructed by an intramolecular Heck annulation of an α, β-unsaturated aryl ester.