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

Chris J. Hamilton; Alan H. Fairlamb; Ian M. Eggleston

doi:10.1039/b110149h

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

Chris J. Hamilton, Alan H. Fairlamb, Ian M. Eggleston (Lead / Corresponding author)

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

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

Original language	English
Pages (from-to)	1115-1123
Number of pages	9
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	2
Issue number	8
DOIs	https://doi.org/10.1039/b110149h
Publication status	Published - 3 Apr 2002

ASJC Scopus subject areas

General Chemistry

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10.1039/b110149h

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title = "Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-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 acrylamidospermidine 5 via a Heck coupling reaction to give the pre-cyclised lunarine derivative 23.",

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Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase. / Hamilton, Chris J.; Fairlamb, Alan H.; Eggleston, Ian M. (Lead / Corresponding author).
In: Journal of the Chemical Society. Perkin Transactions 1, Vol. 2, No. 8, 03.04.2002, p. 1115-1123.

Research output: Contribution to journal › Article › peer-review

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AU - Fairlamb, Alan H.

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

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

Abstract

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