58939-49-4Relevant academic research and scientific papers
A New Synthesis of Coprine and O-Ethylcoprine
Kienzler, Thomas,Strazewski, Peter,Tamm, Christoph
, p. 1078 - 1084 (2007/10/02)
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 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 acidic hydrolysis yielded the 1-aminocyclopropanol hydrochloride (9).Selective cleavage of the amino-protecting group of 8(-> 10 or 11), coupling of the corresponding amine 13 with L-glutamic acid 12, and acidic hydrolysis of the resulting L-glutamine derivative 17 yielded O-ethylcoprine (3) and coprine (1).
