Short-cut bio-inspired synthesis of tricyclic guanidinic motifs of crambescidins and batzelladines marine alkaloids

Amr El-Demerdash, Ludmila Ermolenko, Emmanuelle Gros, Pascal Retailleau, Binh Nguyen Thanh, Anne Gauvin-Bialecki, Ali Al-Mourabit

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    12 Citations (Scopus)

    Abstract

    We report a convenient short synthesis of tricyclic guanidine-containing natural products model featuring four-component reaction between 2,5-dimethoxytetrahydrofuran, 2-aminopyrimidine and two acylacetic or benzoylacetic acids. A synthetic route combining the Robinson–Schöepf bioinspired strategy and biomechanistic analysis of the crambescidin and batzelladine alkaloids family. An application of this strategy to the synthesis of two unnatural stereoisomers of merobatzelladine B is described from the protected guanidine in the form of aminopyrimidine.

    Original languageEnglish
    Pages (from-to)5677-5684
    Number of pages8
    JournalEuropean Journal of Organic Chemistry
    Volume2020
    Issue number35
    Early online date25 Jun 2020
    DOIs
    Publication statusPublished - 22 Sep 2020

    Keywords

    • Batzelladines
    • Bioactivity
    • Crambescidins
    • Guanidine alkaloids
    • Multicomponent reactions

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