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Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.
Hou, Si-Hua; Prichina, Adriana Y; Dong, Guangbin.
Afiliação
  • Hou SH; Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA)s.
  • Prichina AY; Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA)s.
  • Dong G; Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA)s.
Angew Chem Int Ed Engl ; 60(23): 13057-13064, 2021 06 01.
Article em En | MEDLINE | ID: mdl-33822455
Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A, capitalizing on an enantioselective C-C bond activation and a C-O bond cleavage reaction. The rhodium-catalyzed asymmetric "cut-and-sew" transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allowed efficient construction of the fused A/B/C rings and the quaternary center of the natural product. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of boron-mediated ether bond cleavage, we completed the synthesis of the morphine alkaloid (-)-thebainone A by two complementary routes.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides / Morfina Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides / Morfina Idioma: En Ano de publicação: 2021 Tipo de documento: Article