Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine.

Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine.
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DOI:
10.1002/anie.201103198
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发表时间:
2011-08
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影响因子:
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通讯作者:
Peng Chen;X. Bao;Le-Fen Zhang;M. Ding;Xiao-Jie Han;Jing Li;Guo-Biao Zhang;Y. Tu;Chun‐An Fan
Peng Chen;X. Bao;Le-Fen Zhang;M. Ding;Xiao-Jie Han;Jing Li;Guo-Biao Zhang;Y. Tu;Chun‐An Fan
中科院分区:
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文献类型:
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作者:
Peng Chen;X. Bao;Le-Fen Zhang;M. Ding;Xiao-Jie Han;Jing Li;Guo-Biao Zhang;Y. Tu;Chun‐An Fan

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分歧路线:已经发现了一种直接形成C-C键的方法,该方法用于形成存在于生物活性氢化二苯并呋喃生物碱中的关键芳基取代的全碳季立体中心。该方法涉及α-氰基酮与丙烯酸酯的前所未有的有机催化的对映选择性Michael加成,并用于以不对称方式合成标题化合物的新颖且发散的合成策略。
Divergent route: a direct C-C bond-forming approach to the key aryl-substituted all-carbon quaternary stereogenic center present in bioactive hydrodibenzofuran alkaloids has been discovered. This approach involves an unprecedented organocatalytic enantioselective Michael addition of α-cyanoketones with acrylates and was used in a novel and divergent synthetic strategy for the title compounds in asymmetric fashion.