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

Danieli Bruno | Zendy; Lesma Giordano | Zendy; Passarella Daniele | Zendy; Prosperi Davide | Zendy; Sacchetti Alessandro | Zendy; Silvani Alessandra | Zendy; Destro Riccardo | Zendy; May Emanuela | Zendy; Bombardelli Ezio | Zendy

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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

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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