ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-INDOLIZIDINES 209B AND 209D VIA A HIGHLY EFFICIENT AZA-[2,3]-WITTIG REARRANGEMENT OF VINYLAZIRIDINES

Authors
AHMAN J SOMFAI P
Citation
J. Ahman et P. Somfai, ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-INDOLIZIDINES 209B AND 209D VIA A HIGHLY EFFICIENT AZA-[2,3]-WITTIG REARRANGEMENT OF VINYLAZIRIDINES, Tetrahedron, 51(35), 1995, pp. 9747-9756
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
35
Year of publication
1995
Pages
9747 - 9756
Database
ISI
SICI code
0040-4020(1995)51:35<9747:ETSO(2>2.0.ZU;2-T
Abstract
A novel protocol for the enantioselective synthesis of (-)-indolizidin es 209B (2) and 209D (1) is described, in which the key step is the hi ghly efficient aza-[2,3]-Wittig rearrangement of vinylaziridines 11a,b into tetrahydropyridines 12a,b, Functional group manipulation and cha in elongation then gave esters 16a,b which were converted to the targe t alkaloids via lactams 17a,b.