Conformationally Constrained Amino Acids.¹ on the Synthesis of 4-Substituted 8-Membered Cyclic Tryptophan Derivatives

John Y. L. Chung Neuroscience Research Division, Pharmaceutical Discovery, Dept. 47W, Abbott Laboratories, Abbott Park, EL, 60064

James T. Wasicak Neuroscience Research Division, Pharmaceutical Discovery, Dept. 47W, Abbott Laboratories, Abbott Park, EL, 60064

Alex M. Nadzan Neuroscience Research Division, Pharmaceutical Discovery, Dept. 47W, Abbott Laboratories, Abbott Park, EL, 60064

Abstract

The thermal lactamization of 4-(carboethoxy)-methyl-tryptophan ethyl ester (5), prepared from 4-(carboethoxy)methyl-indole 3 via Gilchrist′s method, in refluxing xylene followed by saponification provided the 8-membered cyclic tryptophan derivative 1. Selective reduction of lactam 6 via the iminium ion 9 furnished the cyclic tryptophan derivative 2

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Conformationally Constrained Amino Acids.¹ on the Synthesis of 4-Substituted 8-Membered Cyclic Tryptophan Derivatives

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Conformationally Constrained Amino Acids.1 on the Synthesis of 4-Substituted 8-Membered Cyclic Tryptophan Derivatives

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Conformationally Constrained Amino Acids.¹ on the Synthesis of 4-Substituted 8-Membered Cyclic Tryptophan Derivatives