Tetrahedron Letters

Synthesis of coumarins by ring-closing metathesis using Grubbs' catalyst

TN Van, S Debenedetti, N De Kimpe

Index: Nguyen Van, Tuyen; Debenedetti, Silvia; De Kimpe, Norbert Tetrahedron Letters, 2003 , vol. 44, # 22 p. 4199 - 4201

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Citation Number: 82

Abstract

A novel generally applicable synthesis of coumarins from phenolic substrates utilizing ring- closing metathesis is described. This sequence involves O-allylation of phenols followed by ortho-Claisen rearrangement, subsequent based-induced isomerization affording 2-(1- propenyl) phenols, acylation with acryloyl chloride, and finally ring-closing metathesis (RCM) with Grubbs' second generation catalyst.

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