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Total Synthesis of (+)-Shearilicine.
Kim, Daria E; Zhu, Yingchuan; Harada, Shingo; Aguilar, Isaiah; Cuomo, Abbigayle E; Wang, Minghao; Newhouse, Timothy R.
Afiliação
  • Kim DE; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
  • Zhu Y; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
  • Harada S; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
  • Aguilar I; Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 260-8675, Japan.
  • Cuomo AE; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
  • Wang M; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
  • Newhouse TR; Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
J Am Chem Soc ; 145(8): 4394-4399, 2023 Mar 01.
Article em En | MEDLINE | ID: mdl-36790949
Herein we report the first total synthesis of the indole diterpenoid natural product shearilicine by an 11-step sequence via a generalizable precursor to the highly oxidized subclass of indole diterpenoids. A native chiral auxiliary strategy was employed to access the target molecule in an enantiospecific fashion. The formation of the key carbazole substructure was achieved through a mild intramolecular Heck cyclization, wherein a computational study revealed noncovalent substrate-ligand and ligand-ligand interactions that promoted migratory insertion.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article