AZA-[2,3]-WITTIG REARRANGEMENTS OF VINYLAZIRIDINES AS A NOVEL ENTRY TO INDOLIZIDINE ALKALOIDS - ENANTIOSELECTIVE TOTAL SYNTHESIS OF INDOLIZIDINE 209D

Authors
AHMAN J SOMFAI P
Citation
J. Ahman et P. Somfai, AZA-[2,3]-WITTIG REARRANGEMENTS OF VINYLAZIRIDINES AS A NOVEL ENTRY TO INDOLIZIDINE ALKALOIDS - ENANTIOSELECTIVE TOTAL SYNTHESIS OF INDOLIZIDINE 209D, Tetrahedron letters, 36(2), 1995, pp. 303-306
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
2
Year of publication
1995
Pages
303 - 306
Database
ISI
SICI code
0040-4039(1995)36:2<303:AROVAA>2.0.ZU;2-4
Abstract
An enantioselective total synthesis of indolizidine 209D (1) from epox y alcohol 4 is described. The key step in the sequence involves an aza -[2,3]-Wiltig rearrangement of vinylaziridine 7 to yield the cis-2,6-d isubstituted tetrahydropyridine 8 in 98% yield and as a single detecta ble diastereomer.