Tetrahedron

An improved synthesis of pilocarpine

JI DeGraw

Index: DeGraw,J.I. Tetrahedron, 1972 , vol. 28, p. 967 - 972

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Citation Number: 40

Abstract

Michael condensation of diethyl ethylmalonate with 2-oxo-5-ethoxy-2, 5-dihydrofuran (12) followed by treatment with hot hydrogen bromide-acetic acid afforded 2-ethyl-3- carboxymethylbutenolide (10b). Hydrogenation as the ester (10a) followed by acid hydrolysis yielded dl-homopilopic acid, the key intermediate for the synthesis of pilocarpine.

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