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Synthesis 2014; 46(23): 3199-3206
DOI: 10.1055/s-0034-1378659
DOI: 10.1055/s-0034-1378659
paper
Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling Reactions
Weitere Informationen
Publikationsverlauf
Received: 09. April 2014
Accepted after revision: 25. Juni 2014
Publikationsdatum:
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.
Key words
tabersonine - palladium catalysis - Suzuki–Miyaura cross-coupling reaction - Heck reaction - Sonogashira cross-coupling reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information