Issue 8, 2002

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

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

Supplementary files

Article information

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

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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