AN EFFICIENT APPROACH TOWARD PYRROLIDINYLLACTONE SYSTEM CHARACTERISTIC OF THE STEMONA ALKALOIDS - LEWIS-ACID CATALYZED STEREOSELECTIVE REACTION OF N-BENZYLOXYCARBONYL-2-METHOXYPYRROLIDINE WITH 3-METHYL-2-TRIMETHYLSILYLOXYFURAN

Authors
MORIMOTO Y NISHIDA K HAYASHI Y SHIRAHAMA H
Citation
Y. Morimoto et al., AN EFFICIENT APPROACH TOWARD PYRROLIDINYLLACTONE SYSTEM CHARACTERISTIC OF THE STEMONA ALKALOIDS - LEWIS-ACID CATALYZED STEREOSELECTIVE REACTION OF N-BENZYLOXYCARBONYL-2-METHOXYPYRROLIDINE WITH 3-METHYL-2-TRIMETHYLSILYLOXYFURAN, Tetrahedron letters, 34(36), 1993, pp. 5773-5776
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
36
Year of publication
1993
Pages
5773 - 5776
Database
ISI
SICI code
0040-4039(1993)34:36<5773:AEATPS>2.0.ZU;2-F
Abstract
Pyrrolidinyllactone system 7, common partial structure presented in mo st Stemona alkaloids, was stereoselectively prepared by two-step seque nce: i) syn-selective condensation of N-benzyloxycarbonyl-2-methoxypyr rolidine (8) with 3-methyl-2-trimethylsilyloxyfuran (9) catalyzed by L ewis acids: ii) diastereoselective hydrogenation of the product 10 (Na BH4, NiCl2/MeOH).