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

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.

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Chimie organique Chimie analytique

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CEJ_V2.pdf (918.9 Ko)

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https://hal.science/hal-02998034

Soumis le : mardi 17 novembre 2020-10:09:47

Dernière modification le : jeudi 17 octobre 2024-08:54:33

Archivage à long terme le : jeudi 18 février 2021-18:35:26

Dates et versions

hal-02998034 , version 1 (17-11-2020)

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Paternité - Pas d'utilisation commerciale - Pas de modification

Identifiants

HAL Id : hal-02998034 , version 1
DOI : 10.1002/ejoc.202000744

Citer

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⟩

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