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Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2.1] lactones.
Li, Long; Zhu, Xin-Qi; Zhang, Ying-Qi; Bu, Hao-Zhen; Yuan, Peng; Chen, Jinyu; Su, Jingyi; Deng, Xianming; Ye, Long-Wu.
Afiliação
  • Li L; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
  • Zhu XQ; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
  • Zhang YQ; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
  • Bu HZ; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
  • Yuan P; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
  • Chen J; State Key Laboratory of Cellular Stress Biology , School of Life Sciences , Xiamen University , Xiamen , Fujian 361102 , China.
  • Su J; State Key Laboratory of Cellular Stress Biology , School of Life Sciences , Xiamen University , Xiamen , Fujian 361102 , China.
  • Deng X; State Key Laboratory of Cellular Stress Biology , School of Life Sciences , Xiamen University , Xiamen , Fujian 361102 , China.
  • Ye LW; State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Chemical Biology of Fujian Province , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China . Email: longwuye@xmu.edu.cn.
Chem Sci ; 10(10): 3123-3129, 2019 Mar 14.
Article em En | MEDLINE | ID: mdl-30996895
Alkene carbooxygenation has attracted considerable attention over the past few decades as this approach provides an efficient access to various oxygen-containing molecules, especially the valuable O-heterocycles. However, examples of catalytic alkene carbooxygenation via a direct C-O cleavage are quite scarce, and the C-O cleavage in these cases is invariably initiated by transition metal-catalyzed oxidative addition. We report here a novel Brønsted acid-catalyzed intramolecular alkoxylation-initiated tandem sequence, which represents the first metal-free intramolecular alkoxylation/Claisen rearrangement. Significantly, an unprecedented Brønsted acid-catalyzed intramolecular alkene insertion into the C-O bond via a carbocation pathway was discovered. This method allows the stereocontrolled synthesis of valuable indole-fused bridged [4.2.1] lactones, providing ready access to biologically relevant scaffolds in a single synthetic step from an acyclic precursor. Moreover, such an asymmetric cascade cyclization has also been realized by employing a traceless chiral directing group. Control experiments favor the feasibility of a carbocation pathway for the process. In addition, biological tests showed that some of these newly synthesized indole-fused lactones exhibited their bioactivity as antitumor agents against different breast cancer cells, melanoma cells, and esophageal cancer cells.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article