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Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea-Phosphonium Salt Catalyzed Mannich-Type Reaction.
Pan, Lu; Zheng, Chang-Wu; Fang, Guo-Sheng; Hong, Hao-Ran; Liu, Jun; Yu, Long-Hui; Zhao, Gang.
Afiliação
  • Pan L; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Zheng CW; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Fang GS; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Hong HR; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Liu J; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Yu LH; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
  • Zhao G; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
Chemistry ; 25(25): 6306-6310, 2019 May 02.
Article em En | MEDLINE | ID: mdl-30924207
ABSTRACT
An asymmetric total synthesis of vincadifformine is described. The limited tactics with chiral cation-directed catalysis in total synthesis inspired the development of our strategy for accessing this alkaloid in enantionrich form. The route features a thiourea-phosphonium salt catalyzed Mannich-type reaction, a phosphine-promoted aza-Morita-Baylis-Hillman reaction and a trifluoroacetic acid promoted deprotection/amidation cascade process.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article