ASPIDOSPERMA ALKALOIDS VIA CYCLIZATION OF SECODINE INTERMEDIATE - SYNTHESIS OF (+ -)-3-OXOVINCADIFFORMINE ETHYL-ESTER/

Authors
DANIELI B LESMA G PALMISANO G PASSARELLA D SILVANI A
Citation
B. Danieli et al., ASPIDOSPERMA ALKALOIDS VIA CYCLIZATION OF SECODINE INTERMEDIATE - SYNTHESIS OF (+ -)-3-OXOVINCADIFFORMINE ETHYL-ESTER/, Tetrahedron, 50(23), 1994, pp. 6941-6954
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
23
Year of publication
1994
Pages
6941 - 6954
Database
ISI
SICI code
0040-4020(1994)50:23<6941:AAVCOS>2.0.ZU;2-7
Abstract
(+/-)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular [4 pi+2 pi] cycloaddition of the 3-oxosecodine 13 f irst prepared in turn from the enamide 10 by dehydrogenation with benz eneseleninic anhydride. An insight into the conversion of 10 into 13 w as gained, resulting in the suggestion of a plausible mechanistic path way.