AN EFFICIENT ROUTE TO THE PYRROLIZIDINE RING-SYSTEM VIA AN N-ACYL ANION CYCLIZATION PROCESS

Authors
MURRAY A PROCTOR GR MURRAY PJ
Citation
A. Murray et al., AN EFFICIENT ROUTE TO THE PYRROLIZIDINE RING-SYSTEM VIA AN N-ACYL ANION CYCLIZATION PROCESS, Tetrahedron, 52(10), 1996, pp. 3757-3766
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
10
Year of publication
1996
Pages
3757 - 3766
Database
ISI
SICI code
0040-4020(1996)52:10<3757:AERTTP>2.0.ZU;2-U
Abstract
An enantioselective route to the pyrrolizidine ring system has been de veloped which uses an N-acyl anion cyclisation reaction as the key ste p. This methodology has provided the natural pyrrolizidines (-)-(1R,8S )-1-hydroxypyrrolizidine 7, (-)-pyrrolizidin-1-ene-3-one 9 and (+/-)-t rachelanthamidine 14. Extension of the process to an N-propionyl subst rate provides ready access to a series of 2-methyl pyrrolizidines.