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Tytuł:
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Thiourea-Catalyzed Asymmetric Michael Addition of Carbazolones to 2-Chloroacrylonitrile: Total Synthesis of 5,22-Dioxokopsane, Kopsinidine C, and Demethoxycarbonylkopsin.
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Autorzy:
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Ni D; State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
Wei Y; State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
Ma D; State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
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Źródło:
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Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Aug 06; Vol. 57 (32), pp. 10207-10211. Date of Electronic Publication: 2018 Jul 11.
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Typ publikacji:
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Journal Article
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Język:
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English
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Imprint Name(s):
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Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
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Contributed Indexing:
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Keywords: Michael addition; asymmetric catalysis; indole alkaloids; organocatalysis; total synthesis
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Entry Date(s):
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Date Created: 20180620 Latest Revision: 20191120
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Update Code:
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20240104
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DOI:
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10.1002/anie.201805905
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PMID:
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29920902
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A modified Takemoto catalyst enabled the asymmetric Michael addition of carbazolones to 2-chloroacrylonitrile to afford 3,3-disubstituted carbazolones with excellent enantioselectivity. This method was successfully applied to total syntheses of three Kopsia alkaloids which featured an unprecedented Mn III -mediated oxidative cyclization to create the caged ring system and a SmI 2 -mediated reductive coupling as key steps.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
