Short-Cut Bio-Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids

Amr El-Demerdash (1) , Ludmila Ermolenko (1) , Emmanuelle Gros (2) , Pascal Retailleau (1) , T .B. Nguyen (1) , Anne Gauvin-Bialecki (2) , Ali Al-Mourabit (1)

1 ICSN - Institut de Chimie des Substances Naturelles
2 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments

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.

Domaines: Chimie organique; Chimie analytique

Amr El-Demerdash, Ludmila Ermolenko, Emmanuelle Gros, Pascal Retailleau, T .B. Nguyen, et al.. Short-Cut Bio-Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids. European Journal of Organic Chemistry, 2020, 18 (5), pp.272. ⟨10.1002/ejoc.202000744⟩. ⟨hal-02998034⟩