Helvetica chimica acta

A New Synthesis of Coprine and O??Ethylcoprine

T Kienzler, P Strazewski, C Tamm

Index: Kienzler, Thomas; Strazewski, Peter; Tamm, Christoph Helvetica Chimica Acta, 1992 , vol. 75, # 4 p. 1078 - 1084

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Citation Number: 10

Abstract

Abstract Coprine (1), a toxine of the mushroom Coprinus atramentarius, was synthesized starting from the 2-amino and 1-carboxy-protected L-glutamic acids 4 and 12. Compound 4 was first decarboxylated by a radical chain reaction to bromide 5 which underwent ring closure to cyclopropanecarboxylate 6 on treatment with NaH (Scheme 1). Subsequent oxidative electrolysis of 7 to form tert-butyl N-(1-ethoxycyclopropyl) carbamate (8) and ...