A New Synthesis of Coprine and O-Ethylcoprine

✍ Scribed by Thomas Kienzler; Peter Strazewski; Christoph Tamm

• Book ID: 102258102
• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: German
• Weight: 484 KB
• Volume: 75
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19920750411

✦ Synopsis

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 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).