Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative - Archive ouverte HAL
Article Dans Une Revue Angewandte Chemie International Edition Année : 2020

Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative

Résumé

The first total synthesis of the caged monoterpene indole alkaloid cymoside is reported. This natural product displays a unique hexacyclic-fused skeleton whose biosynthesis implies an early oxidative cyclisation of strictosidine. Our approach to the furo[3,2-b]indoline framework relied on an unprecedented biomimetic sequence which started by the diastereoselective oxidation of the indole ring into a hydroxyindolenine which triggered the addition of an enol ether and was followed by the trapping of an oxocarbenium intermediate.

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Dates et versions

hal-02471140 , version 1 (12-11-2020)

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Yingchao Dou, Cyrille Kouklovsky, Vincent Gandon, Guillaume Vincent. Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative. Angewandte Chemie International Edition, 2020, 59 (4), pp.1527-1531. ⟨10.1002/anie.201912812⟩. ⟨hal-02471140⟩
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