Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

Martin G. Banwell*, Curtis F. Crasto, Christopher J. Easton, Tomislav Karoli, Darren R. March, Michael R. Nairn, Peter J. O’hanlon, Mark D. Oldham, Anthony C. Willis, Weimin Yue

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    22 Citations (Scopus)

    Abstract

    The ketone (±)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (2)−21 and (+)−21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

    Original languageEnglish
    Pages (from-to)2210-2211
    Number of pages2
    JournalChemical Communications
    Volume1
    Issue number21
    DOIs
    Publication statusPublished - 2001

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