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)

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    29 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 languageEnglish
    Pages (from-to)1115-1123
    Number of pages9
    JournalJournal of the Chemical Society. Perkin Transactions 1
    Volume2
    Issue number8
    DOIs
    Publication statusPublished - 3 Apr 2002

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