Useful synthesis of. alpha.,. beta.-dehydrotryptophan derivatives

…, N Yoneda, M Miyoshi, K Matsumoto

Index: Moriya, Tamon; Yoneda, Naoto; Miyoshi, Muneji; Matsumoto, Kazuo Journal of Organic Chemistry, 1982 , vol. 47, # 1 p. 94 - 98

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Citation Number: 21

Abstract

N-Acyl-a@-dehydrotryptophan (ATrp) esters 4a-h were directly synthesized by the reaction of 3-[(1-pyrrolidinyl) methylene]-3H-indole (2) with N-acylglycinates 3a-h in reasonable yields. Of these, N-formylsubstituted ATrp methyl ester (4a) was easily converted into ATrp methyl ester (7) in a high yield by acidolysis with dry methanol-hydrogen chloride. Furthermore, 7 was successfully used for the preparation of a dipeptide, N-alanyl- ...