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.
New tetracyclic colchicinoids from the reaction of N-deacetylthiocolchicine and N-deacetylcolchicine with nitrous acid and tert-butyl nitrite / B. Danieli, G. Lesma, D. Passarella, D. Prosperi, A. Sacchetti, A. Silvani, R. Destro, E. May, E. Bombardelli. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 86:6(2003), pp. 2082-2089. [10.1002/hlca.200390164]
New tetracyclic colchicinoids from the reaction of N-deacetylthiocolchicine and N-deacetylcolchicine with nitrous acid and tert-butyl nitrite
B. DanieliPrimo
;G. LesmaSecondo
;D. Passarella;A. Silvani;R. Destro;
2003
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.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
