Bioinspired Divergent Oxidative Cyclization from Strictosidine and Vincoside Derivatives: Second Generation Total Synthesis of Cymoside and Access to an Original Hexacyclic‐Fused Furo[3,2‐b]indoline - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2020

Bioinspired Divergent Oxidative Cyclization from Strictosidine and Vincoside Derivatives: Second Generation Total Synthesis of Cymoside and Access to an Original Hexacyclic‐Fused Furo[3,2‐b]indoline

Résumé

We report our second generation synthesis of (-)-cymoside as well as the formation of a new hexacyclic-fused furo[3,2-b]indoline framework. After a Pictet-Spengler condensation between secologanin tetraacetate and tryptamine, the course of the cyclization of the 7-hydroxyindolenine intermediate generated by oxidation with an oxaziridine, depends on the stereochemistry of the 3-position. The 3-(S)-strictosidine stereochemistry delivered efficiently the scaffold of cymoside via intramolecular coupling with the C16-C17 enol ether, while the 3-(R)-vincoside stereochemistry directed towards the reaction with the C18-C19 terminal alkene and the formation of the unexpected caged compound.

Domaines

Chimie
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Dates et versions

hal-02960522 , version 1 (12-11-2020)

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Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent. Bioinspired Divergent Oxidative Cyclization from Strictosidine and Vincoside Derivatives: Second Generation Total Synthesis of Cymoside and Access to an Original Hexacyclic‐Fused Furo[3,2‐b]indoline. Chemistry - A European Journal, 2020, 26 (71), pp.17190-17194. ⟨10.1002/chem.202003758⟩. ⟨hal-02960522⟩
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