Synthesis of new bridged tetrahydro-beta-carbolines and spiro-fused quinuclidines

Authors
Burm, BEA Gremmen, C Wanner, MJ Koomen, GJ
Citation
Bea. Burm et al., Synthesis of new bridged tetrahydro-beta-carbolines and spiro-fused quinuclidines, TETRAHEDRON, 57(10), 2001, pp. 2039-2049
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
10
Year of publication
2001
Pages
2039 - 2049
Database
ISI
SICI code
0040-4020(20010303)57:10<2039:SONBTA>2.0.ZU;2-F
Abstract
Two series of chemically related, conformationally restricted ring systems were synthesized. Bridged tetrahydro-beta -carbolines, designed as selectiv e 5-HT receptor ligands, were formed via Pictet-Spengler condensation of cy clic tryptamine precursors. Oxidation of the indole 2-position of the precu rsors followed by condensation with aldehydes produced spiro-cyclic quinucl idines, containing important muscarine receptor pharmacophores. (C) 2001 El sevier Science Ltd. All rights reserved.