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 , Erik Van der Eycken .

Journal Name: Combinatorial Chemistry & High Throughput Screening

Volume 10 , Issue 9 , 2007

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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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Article Details

Year: 2007
Page: [790 - 801]
Pages: 12
DOI: 10.2174/138620707783018513
Price: $58

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