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Issue 22, 2001
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Stereoselective synthesis of the pyrroloisoquinoline ring system

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Abstract

In this paper we report a facile and stereoselective approach to the pyrroloisoquinoline ring system through the application of N-acyliminium chemistry from readily available non-racemic chiral templates. The stereochemical outcome of the cyclisation reactions has been determined by NOE and X-ray crystallography. We also demonstrate the synthetic potential of our new approach through removal of the pendant hydroxymethyl auxiliary from a product of cyclisation.

Graphical abstract: Stereoselective synthesis of the pyrroloisoquinoline ring system

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Article information


Submitted
20 Jun 2001
Accepted
13 Sep 2001
First published
25 Oct 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3029-3036
Article type
Paper

Stereoselective synthesis of the pyrroloisoquinoline ring system

S. M. Allin, S. L. James, W. P. Martin, T. A. D. Smith and M. R. J. Elsegood, J. Chem. Soc., Perkin Trans. 1, 2001, 3029
DOI: 10.1039/B105402N

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