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Asymmetric Total Synthesis of Cerorubenic Acid-III.
Liu, Xin; Liu, Junyang; Wu, Jianlei; Huang, Guocheng; Liang, Rong; Chung, Lung Wa; Li, Chuang-Chuang.
Afiliação
  • Liu X; Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
  • Liu J; Institute of Chinese Medical Sciences , University of Macau , Macau , China.
  • Wu J; Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
  • Huang G; Academy for Advanced Interdisciplinary Studies , Southern University of Science and Technology (SUSTech) , Shenzhen 518055 , China.
  • Liang R; Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
  • Chung LW; Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
  • Li CC; Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
J Am Chem Soc ; 141(7): 2872-2877, 2019 02 20.
Article em En | MEDLINE | ID: mdl-30721058
ABSTRACT
The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article