Intramolecular Diels−Alder Reactions of 3-(Tetrahydropyridinyl)indoles:  Stereoselective Synthesis of Novel Pentacyclic Ring Systems

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 t...

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Published in:Journal of organic chemistry 1998-03, Vol.63 (6), p.1974-1980
Main Authors: Gharagozloo, Parviz, Miyauchi, Masao, Birdsall, Berry, Birdsall, Nigel J. M
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Language:English
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container_end_page 1980
container_issue 6
container_start_page 1974
container_title Journal of organic chemistry
container_volume 63
creator Gharagozloo, Parviz
Miyauchi, Masao
Birdsall, Berry
Birdsall, Nigel J. M
description 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.
doi_str_mv 10.1021/jo971981+
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title Intramolecular Diels−Alder Reactions of 3-(Tetrahydropyridinyl)indoles:  Stereoselective Synthesis of Novel Pentacyclic Ring Systems
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