Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach - Archive ouverte HAL
Article Dans Une Revue Angewandte Chemie International Edition Année : 2023

Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach

Résumé

We report a synthetic endeavor towards the highly strained pentacyclic caged framework of the mavacuran alkaloids which culminated with the concise total synthesis of C-fluorocurine, C-profluorocurine, C-mavacurine, normavacurine, 16-epi-pleiocarpamine and taberdivarine H. We designed an original strategy which involves a late stage construction of the D ring via a Michael addition of a vinylic nucleophile to a 2-indolyl acrylate moiety. While the intramolecular Michael addition did not succeed, we were able to perform a diastereoselective unusual intermolecular 1,4-addition of a functionalized vinyl lithium reagent onto a readily accessible Michael acceptor. Final cyclization was achieved via nucleophilic substitution into an ammo-nium intermediate. The first total syntheses of C-profluorocurine and C-fluorocurine were finalized via respectively the dihy-droxylation of C-mavacurine and a pinacol rearrangement.

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Chimie
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Dates et versions

hal-04274088 , version 1 (07-11-2023)

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Audrey Mauger, Maxime Jarret, Aurélien Tap, Rémi Perrin, Régis Guillot,, et al.. Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach. Angewandte Chemie International Edition, 2023, 62, ⟨10.1002/anie.202302461⟩. ⟨hal-04274088⟩
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