Enantiocontrolled preparation of indolizidines: Synthesis of (-)-2-epilentiginosine and (+)-lentiginosine

Authors
Rasmussen, MO Delair, P Greene, AE
Citation
Mo. Rasmussen et al., Enantiocontrolled preparation of indolizidines: Synthesis of (-)-2-epilentiginosine and (+)-lentiginosine, J ORG CHEM, 66(16), 2001, pp. 5438-5443
Citations number
48
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
16
Year of publication
2001
Pages
5438 - 5443
Database
ISI
SICI code
0022-3263(20010810)66:16<5438:EPOISO>2.0.ZU;2-H
Abstract
A highly stereoselective approach to (-)-2-epilentiginosine and (+)-lentigi nosine has been developed based on a diastereofacially selective cycloaddit ion of dichloroketene with a chiral dienol ether. The two naturally occurri ng indolizidines are each obtained enantioselectively (greater than or equa l to 99:1) in ca. 8.5% overall yield.