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

Hamilton, Chris J., Fairlamb, Alan H. and Eggleston, Ian M. (2002) Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (+/-)-lunarine, a time-dependent inhibitor of trypanothione reductase. Journal of the Chemical Society, Perkin Transactions 1, 1 (8). pp. 1115-1123. ISSN 1472-7781

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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 acrylamidospermidine dagger 5 via a Heck coupling reaction to give the pre-cyclised lunarine derivative 23.

Item Type:	Article
Uncontrolled Keywords:	reagents,alkyl aryl ethers,nitriles,cleavage,oxidative stress,lunarine
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User:	Rachel Smith
Date Deposited:	18 May 2011 09:38
Last Modified:	24 Sep 2024 10:17
URI:	https://ueaeprints.uea.ac.uk/id/eprint/30698
DOI:	10.1039/b110149h

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