Tetrahedron

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

BEA Burm, C Gremmen, MJ Wanner, GJ Koomen

Index: Burm, Brigitte E.A; Gremmen, Christiaan; Wanner, Martin J; Koomen, Gerrit-Jan Tetrahedron, 2001 , vol. 57, # 10 p. 2039 - 2049

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Citation Number: 9

Abstract

Two series of chemically related, conformationally restricted ring systems were synthesized. Bridged tetrahydro-β-carbolines, designed as selective 5-HT receptor ligands, were formed via Pictet–Spengler condensation of cyclic tryptamine precursors. Oxidation of the indole 2- position of the precursors followed by condensation with aldehydes produced spiro-cyclic quinuclidines, containing important muscarine receptor pharmacophores.