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New Tetracyclic Colchicinoids from the Reaction of N ‐Deacetylthiocolchicine and N ‐Deacetylcolchicine with Nitrous Acid and tert ‐Butyl Nitrite
Author(s) -
Danieli Bruno,
Lesma Giordano,
Passarella Daniele,
Prosperi Davide,
Sacchetti Alessandro,
Silvani Alessandra,
Destro Riccardo,
May Emanuela,
Bombardelli Ezio
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390164
Subject(s) - chemistry , nitrous acid , stereocenter , nitrite , medicinal chemistry , stereochemistry , organic chemistry , nitrate , catalysis , enantioselective synthesis
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.