Synthesis 2014; 46(23): 3199-3206
DOI: 10.1055/s-0034-1378659
paper
© Georg Thieme Verlag Stuttgart · New York

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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Received: 09. April 2014

Accepted after revision: 25. Juni 2014

Publikationsdatum:
27. August 2014 (online)


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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.

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