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New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite

✍ Scribed by Bruno Danieli; Giordano Lesma; Daniele Passarella; Davide Prosperi; Alessandro Sacchetti; Alessandra Silvani; Riccardo Destro; Emanuela May; Ezio Bombardelli

Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 114 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390164

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✦ Synopsis

Abstract

Reaction of N‐deacetylthiocolchicine (3) and N‐deacetylcolchicine (4) with nitrous acid (HONO) furnished the new tetracyclic colchicinoids 5 and 6, as well as the Demyanov‐rearrangement products 7 and 8. Starting from 3, the pyrazole‐containing tetracycle 9 was obtained. The novel compounds were characterized spectroscopically, and an X‐ray crystal‐structure analysis of 5 allowed us to establish the absolute configurations at the stereogenic centers.

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