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

Hussein Abou-Hamdan, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent

The Journal of organic chemistry 2021 Jul 02

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

Citation

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. The Journal of organic chemistry. 2021 Jul 02;86(13):9244-9252