Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling­ Reactions

Fanglei Chen; Min Lei; Lihong Hu

doi:10.1055/s-0034-1378659

Synthesis, Table of Contents

Synthesis 2014; 46(23): 3199-3206
DOI: 10.1055/s-0034-1378659

paper

Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling Reactions

Fanglei Chen

Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai, 201203, P. R. of China Fax: +86(21)20231965 Email: mlei@simm.ac.cn Email: lhhu@simm.ac.cn

,

Min Lei*

Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai, 201203, P. R. of China Fax: +86(21)20231965 Email: mlei@simm.ac.cn Email: lhhu@simm.ac.cn

,

Lihong Hu*

Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai, 201203, P. R. of China Fax: +86(21)20231965 Email: mlei@simm.ac.cn Email: lhhu@simm.ac.cn

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Abstract

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Abstract

A series of C-10-substituted tabersonine analogues have been synthesized via palladium-catalyzed cross-coupling reactions. To be specific, tabersonine reacted with NIS in TFA to generate the 10-iodotabersonine, which participated in palladium-catalyzed or palladium/copper co-catalyzed cross-coupling reactions, such as Suzuki–Miyaura cross-coupling reaction, Heck reaction, and Sonogashira cross-coupling reaction, to afford C-10 tabersonine analogues. These protocols provide the possibility of introducing substituents with structural diversity and complexity into the C-10 of tabersonine for the pharmacological activity screening.

Key words

tabersonine - palladium catalysis - Suzuki–Miyaura cross-coupling reaction - Heck reaction - Sonogashira cross-coupling reaction

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References

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Supplementary Material

Supporting Information

Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling­ Reactions

Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling Reactions