Toward General Access to the Aspidosperma-Type Terpenoid Indole Alkaloids: Synthesis of the Key 3,3-Disubstituted Piperidones through Enantioselective Intramolecular Heck-Type Reaction of Chloroformamides

Yoshizumi Yasui; Hiroshi Takeda; Yoshiji Takemoto

doi:10.1248/cpb.56.1567

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Toward General Access to the Aspidosperma-Type Terpenoid Indole Alkaloids: Synthesis of the Key 3,3-Disubstituted Piperidones through Enantioselective Intramolecular Heck-Type Reaction of Chloroformamides

Yoshizumi Yasui, Hiroshi Takeda, Yoshiji Takemoto

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Keywords: enantioselective reaction, total synthesis, terpenoid indole alkaloid

JOURNAL FREE ACCESS

2008 Volume 56 Issue 11 Pages 1567-1574

DOI https://doi.org/10.1248/cpb.56.1567

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Abstract

An enantioselective intramolecular Heck-type reaction of chloroformamides has been developed for the synthesis of 3,3-disubstituted piperidones. The desired piperidone was formed in the presence of a palladium catalyst, an optically active phosphoramidite ligand, K₃PO₄ and Ag₃PO₄. The obtained piperidone was converted to epieburnamonine.

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