TOTAL SYNTHESIS OF (+ -)-MONOMORINE-I AND (+/-)-INDOLIZIDINE 195B BY AN AZA-[2,3]-WITTIG REARRANGEMENT OF A VINYLAZIRIDINE/

Authors
SOMFAI P JAREVANG T LINDSTROM UM SVENSSON A
Citation
P. Somfai et al., TOTAL SYNTHESIS OF (+ -)-MONOMORINE-I AND (+/-)-INDOLIZIDINE 195B BY AN AZA-[2,3]-WITTIG REARRANGEMENT OF A VINYLAZIRIDINE/, Acta chemica Scandinavica, 51(10), 1997, pp. 1024-1029
Citations number
18
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
51
Issue
10
Year of publication
1997
Pages
1024 - 1029
Database
ISI
SICI code
0904-213X(1997)51:10<1024:TSO(-A>2.0.ZU;2-K
Abstract
A novel synthesis of (+/-)-monomorine I(1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2 ,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be c onverted into the target alkaloids by reductive amination (1:2 1.5:1).