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
› Author Affiliations
Further Information

Publication History

Received: 09 April 2014

Accepted after revision: 25 June 2014

Publication Date:
27 August 2014 (online)


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.

Supporting Information