Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

Authors
Becker, DP Husa, RK Moormann, AE Villamil, CI Flynn, DL
Citation
Dp. Becker et al., Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491, TETRAHEDRON, 55(40), 1999, pp. 11787-11802
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
40
Year of publication
1999
Pages
11787 - 11802
Database
ISI
SICI code
0040-4020(19991001)55:40<11787:ESOD5S>2.0.ZU;2-4
Abstract
A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamo to's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetri c synthesis of azanoradamantane benzamide SC-52491 was carried out employin g Helmchen's asymmetric Diels-Alder methodology to construct all four conti guous asymmetric centers with the correct relative stereochemistry and in 9 9.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.