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

Peng Chen, Xu Bao, Le-Fen Zhang, Ming Ding, Xiao-Jie Han, Jing Li, Guo-Biao Zhang, Yong-Qiang Tu, Chun-An Fan

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Tianshui Nanlu, China.

Angewandte Chemie (International ed. in English) 2011 Aug 22

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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. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Peng Chen, Xu Bao, Le-Fen Zhang, Ming Ding, Xiao-Jie Han, Jing Li, Guo-Biao Zhang, Yong-Qiang Tu, Chun-An Fan. Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine. Angewandte Chemie (International ed. in English). 2011 Aug 22;50(35):8161-6