Synthesis of a Seco iso -Secologanin Aglycone Analogue of Interest toward Secoiridoids and Monoterpene Indole Alkaloids - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Synthesis of a Seco iso -Secologanin Aglycone Analogue of Interest toward Secoiridoids and Monoterpene Indole Alkaloids

Résumé

We report the access to an acyclic iso-secologanin aglycone analogue relevant to seco-iridois and monoterpene indole alkaloids. Its synthesis involved a regioselective allylic alkylation of a linear dienyl carbonate with dimethyl malonate catalyzed by an iridium complex and an anti-Markovnikov Wacker-type oxidation of the terminal alkene of the branched product obtained. The aldehyde thus formed was engaged in a Pictet-Spengler reaction with tryptamine towards monoterpene indole alkaloids.

Domaines

Chimie organique
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Dates et versions

hal-03286160 , version 1 (13-07-2021)

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Hussein Abou-Hamdan, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent. Synthesis of a Seco iso -Secologanin Aglycone Analogue of Interest toward Secoiridoids and Monoterpene Indole Alkaloids. Journal of Organic Chemistry, 2021, 86 (13), pp.9244-9252. ⟨10.1021/acs.joc.1c00916⟩. ⟨hal-03286160⟩
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