Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide

Authors
Goti, A Cacciarini, M Cardona, F Cordero, FM Brandi, A
Citation
A. Goti et al., Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide, ORG LETT, 3(9), 2001, pp. 1367-1369
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
9
Year of publication
2001
Pages
1367 - 1369
Database
ISI
SICI code
1523-7060(20010503)3:9<1367:TSO(BI>2.0.ZU;2-X
Abstract
[GRAPHICS] Straightforward total syntheses of (-)-rosmarinecine have been achieved fro m L-malic acid derived pyrroline N-oxides by two novel useful cascade proce sses, which join the family of domino reactions. Both strategies, which fur nished the target alkaloid in enantioenriched and enantiopure forms, respec tively, allow complete control of configuration at all the three newly crea ted contiguous stereogenic centers.