Intramolecular Diels−Alder Reactions of 3-(Tetrahydropyridinyl)indoles: Stereoselective Synthesis of Novel Pentacyclic Ring Systems
journal contributionposted on 28.02.1998, 00:00 authored by Parviz Gharagozloo, Masao Miyauchi, Berry Birdsall, Nigel J. M. Birdsall
Intramolecular Diels−Alder cycloaddition reactions of 1-(4-pentenoyl)-3-(tetrahydropyridinyl)indoles 7 followed by acid-catalyzed double-bond migration result in the stereoselective formation of novel pentaheterocyclic ring systems related to those of certain Strychnos alkaloids. The assignment of the stereochemistry of the cycloadducts was based on the analysis of 1D and 2D DQF−COSY and ROESY 1H NMR spectra. 1-(4-Pentynoyl)-3-(tetrahydropyridinyl)indoles underwent an analogous cyclization to give the corresponding pentacyclic carbazoles in high yields.
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Strychnos alkaloidsnovel pentaheterocyclic ring systemspentenoylanalysiscycloadditionyieldDielcyclizationROESY 1 H NMR spectraPentacyclicstereochemistryPentynoylSynthesiassignmentDQFcycloadduct1 Dpentacyclic carbazolesstereoselective formationStereoselectiveTetrahydropyridinylIntramolecularmigration