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Combinatorial Chemistry & High Throughput Screening


ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

Suzuki-Miyaura and Stille Reactions as Key Steps in the Synthesis of Diversely Functionalized Amaryllidaceae Alkaloid Analogs Bearing a 5,6,7,8-Tetrahydrobenzo[c,e]Azocine Skeleton

Author(s): Prasad Appukkuttan, Wim Dehaen and Erik Van der Eycken

Volume 10, Issue 9, 2007

Page: [790 - 801] Pages: 12

DOI: 10.2174/138620707783018513

Price: $65


Microwave-assisted Suzuki-Miyaura and Stille cross-coupling reactions for the synthesis of highly electronrich and diversely functionalized biaryl intermediates are presented. Microwave-irradiation has been demonstrated to be a very powerful tool for performing difficult transition metal-catalyzed cross-coupling reactions with unfavorably substituted coupling partners. The key biaryl intermediates were used for the microwave-enhanced construction of the 5,6,7,8- tetrahydrobenzo[c,e]azocine skeleton of the Apogalanthamine analogs. The success of the strategy is demonstrated by synthesizing a number of hitherto unknown, diversely functionalized, natural product analogs.

Keywords: Suzuki-Miyaura, stille, cross-coupling, biaryl, natural products, microwave

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