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Article Dans Une Revue Organic Letters Année : 2024

Total Synthesis of Cyclotripeptidic Natural Products Anacine, Aurantiomide C, Polonimides A and C, and Verrucine F

Résumé

The total synthesis of cyclotripeptidic natural products possessing a central piperazino[2,1-b]quinazolin-3,6-dione core is described through an original strategy involving the pivotal cyclocondensation of an electrophilic homoserine lactone intermediate. The alkylidene group was spontaneously installed by autoxidation during the cyclocondensation process, while the propionamide side chain was introduced through the nickel-catalyzed aminocarbonylation of a bromoethyl intermediate. This last reaction is unprecedented on such highly functionalized intermediates. Finally, we explored structural modifications and interconversions of the natural products. Overall, this work led to anacine, aurantiomide C, polonimides A and C, and verrucine F.
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hal-04575245 , version 1 (14-05-2024)

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Guanghui Han, Wei Zhang, Emmanuelle Acs, Alexis Paquin, Quentin Ronzon, et al.. Total Synthesis of Cyclotripeptidic Natural Products Anacine, Aurantiomide C, Polonimides A and C, and Verrucine F. Organic Letters, 2024, 26 (13), pp.2629-2634. ⟨10.1021/acs.orglett.4c00658⟩. ⟨hal-04575245⟩
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