A formal synthesis of (+/-)-eseroline via an azaoxy-cope rearrangement

Authors
Santos, PF Almeida, PS Lobo, AM Prabhakar, S
Citation
Pf. Santos et al., A formal synthesis of (+/-)-eseroline via an azaoxy-cope rearrangement, HETEROCYCLE, 55(6), 2001, pp. 1029-1043
Citations number
52
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
6
Year of publication
2001
Pages
1029 - 1043
Database
ISI
SICI code
0385-5414(20010601)55:6<1029:AFSO(V>2.0.ZU;2-H
Abstract
A novel synthesis of (+/-)-desoxyeseroline, from the crucial oxindole (15), obtained by a 3,3-sigmatropic rearrangement of the enolate derived from th e hydroxamic acid derivative (5) followed by radical desulfurisation, has b een described. The requisite C2N fragment has been introduced through a Mic hael addition of nitroethylene to 15.