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The Total Synthesis of (-)-Scabrolide A.
Hafeman, Nicholas J; Loskot, Steven A; Reimann, Christopher E; Pritchett, Beau P; Virgil, Scott C; Stoltz, Brian M.
Afiliação
  • Hafeman NJ; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
  • Loskot SA; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
  • Reimann CE; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
  • Pritchett BP; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
  • Virgil SC; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
  • Stoltz BM; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.
J Am Chem Soc ; 142(19): 8585-8590, 2020 05 13.
Article em En | MEDLINE | ID: mdl-32223255
The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels-Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5-6-7] linear carbocyclic core of the molecule and complete the total synthesis.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
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XML
PubMed Links
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Estados Unidos