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

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

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27 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 languageEnglish
Pages (from-to)1115-1123
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume1
Issue number8
DOIs
Publication statusPublished - 2002

Keywords

  • REAGENTS
  • ALKYL ARYL ETHERS
  • NITRILES
  • CLEAVAGE
  • OXIDATIVE STRESS
  • LUNARINE

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