Asymmetric synthesis of (-)-indolizidines 167B and 209D based on stereocontrolled allylation of a chiral tricyclic N-acyl-N,O-acetal

Authors
Yamazaki, N Ito, T Kibayashi, C
Citation
N. Yamazaki et al., Asymmetric synthesis of (-)-indolizidines 167B and 209D based on stereocontrolled allylation of a chiral tricyclic N-acyl-N,O-acetal, ORG LETT, 2(4), 2000, pp. 465-467
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
4
Year of publication
2000
Pages
465 - 467
Database
ISI
SICI code
1523-7060(20000224)2:4<465:ASO(1A>2.0.ZU;2-P
Abstract
[GRAPHICS] The tricyclic N-acyl-N,O-acetal incorporating (S)-2-(1-aminoethyl)phenol as a chiral auxiliary underwent TiCl4-mediated allylation to give the chiral (5S)-allylpyrrolidinone with retention of configuration in high yield and d iastereoselectivity. On the bases of this methodology, the asymmetric synth eses of the dendrobatid alkaloids (-)-indolizidines 167B and 209D were achi eved.