Issue 8, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regiocontrolled synthesis of the macrocyclic polyaminealkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase

Chris J. Hamilton,a   Alan H. Fairlambb  and  Ian M. Eggleston*a  

* Corresponding authors

a Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, Carnelley Building, University of Dundee, Dundee, UK

b Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, Wellcome Trust Biocentre, University of Dundee, Dundee, UK

Abstract

A regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine is described. The key steps involve the preparation of the differentially functionalised cis-3-oxo-8-bromo-9b-cyano-1,2,3,4,4a,9b-hexahydrobenzofuranyl tricyclic scaffold 14 which, following further elaboration, is coupled to the selectively protected acrylamidospermidine5via a Heck coupling reaction to give the pre-cyclised lunarine derivative 23.

Graphical abstract: Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase

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Article information

DOI
https://doi.org/10.1039/B110149H
Article type
Paper
Submitted
09 Nov 2001
Accepted
26 Feb 2002
First published
03 Apr 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1115-1123

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Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase

C. J. Hamilton, A. H. Fairlamb and I. M. Eggleston, J. Chem. Soc., Perkin Trans. 1, 2002, 1115 DOI: 10.1039/B110149H

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