Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2-acetoxy-butyrolactones

Authors
Enders, D Sun, HB Leusink, FR
Citation
D. Enders et al., Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2-acetoxy-butyrolactones, TETRAHEDRON, 55(19), 1999, pp. 6129-6138
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
19
Year of publication
1999
Pages
6129 - 6138
Database
ISI
SICI code
0040-4020(19990507)55:19<6129:DAESO4>2.0.ZU;2-F
Abstract
An efficient asymmetric synthesis of 4-mono- and 3,4-disubstituted 2-acetox y-butyrolactones 2 has been developed, based on a hydrazone-mediated asymme tric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this proces s in the synthesis of the natural hunger substance 3 (ee = 90%) is also pre sented, (C) 1999 Elsevier Science Ltd. All rights reserved.