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

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 dagger 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	1
Issue number	8
DOIs	https://doi.org/10.1039/b110149h
Publication status	Published - 2002

Keywords

REAGENTS
ALKYL ARYL ETHERS
NITRILES
CLEAVAGE
OXIDATIVE STRESS
LUNARINE

Access to Document

10.1039/b110149h

Cite this

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

keywords = "REAGENTS, ALKYL ARYL ETHERS, NITRILES, CLEAVAGE, OXIDATIVE STRESS, LUNARINE",

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year = "2002",

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T1 - Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (+/-)-lunarine, a time-dependent inhibitor of trypanothione reductase

AU - Hamilton, Chris J.

AU - Fairlamb, Alan H.

AU - Eggleston, Ian M.

PY - 2002

Y1 - 2002

N2 - 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.

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

KW - REAGENTS

KW - ALKYL ARYL ETHERS

KW - NITRILES

KW - CLEAVAGE

KW - OXIDATIVE STRESS

KW - LUNARINE

U2 - 10.1039/b110149h

DO - 10.1039/b110149h

M3 - Article

SN - 1472-7781

VL - 1

SP - 1115

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 8

ER -