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Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler-Napieralski/Semipinacol Rearrangement Reaction.
Wang, Shuang-Hu; Si, Rui-Qi; Zhuang, Qing-Bo; Guo, Xiang; Ke, Tian; Zhang, Xiao-Ming; Zhang, Fu-Min; Tu, Yong-Qiang.
Afiliação
  • Wang SH; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Si RQ; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Zhuang QB; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Guo X; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Ke T; School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.
  • Zhang XM; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Zhang FM; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
  • Tu YQ; State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.
Angew Chem Int Ed Engl ; 59(49): 21954-21958, 2020 12 01.
Article em En | MEDLINE | ID: mdl-32851781
ABSTRACT
A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article