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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