A straightforward route to enantiopure pyrrolizidines and indolizidines bycycloaddition to pyrroline N-oxides derived from the chiral pool

Citation
A. Goti et al., A straightforward route to enantiopure pyrrolizidines and indolizidines bycycloaddition to pyrroline N-oxides derived from the chiral pool, MOLECULES, 4(1), 1999, pp. 1-12
Citations number
65
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
4
Issue
1
Year of publication
1999
Pages
1 - 12
Database
ISI
SICI code
1420-3049(199901)4:1<1:ASRTEP>2.0.ZU;2-1
Abstract
Enantiomerically pure, five membered cyclic nitrones, easily obtained in la rge amounts from protected hydroxyacids and aminoacids such as D- and L-tar taric, L-malic, and L-aspartic acids, give cycloaddition reactions with a g ood diastereocontrol. The adducts of L-malic and L-aspartic acids derived f rom addition of nitrones to dimethyl maleate and gamma-crotonolactone were easily converted into enantiopure pyrrolizidinones, which can be transforme d into polyhydroxypyrrolidines or polyhydroxypyrrolizidines, both interesti ng compounds as potential glycosidase inhibitors. The method is suitable fo r natural products synthesis as exemplified by a straightforward and conven ient access to the pyrrolizidine alkaloid necine base (-)-hastanecine, as w ell as to indolizidine alkaloids, i.e. (+)-lentiginosine.