Vicinal all-carbon quaternary stereocenters are widely present in natural products and bioactive molecules.However,the construction of such motif in one step from readily available starting materials remains a signifi...Vicinal all-carbon quaternary stereocenters are widely present in natural products and bioactive molecules.However,the construction of such motif in one step from readily available starting materials remains a significant challenge.Herein,we report a phosphine-catalyzed divergent γ,γ-and ε,γ-umpolung domino addition of bisoxindoles with allenoates.This method serves as a practical tool for the concise synthesis of a series of bisoxindole derivatives bearing sterically hindered vicinal all-carbon quaternary stereocenters under mild reaction conditions.The applicability of this novel method was demonstrated with the gram-scale synthesis of three known advanced intermediates for the total syntheses of calycanthine,chimonanthine and folicanthine.展开更多
基金the financial support provided by the National Natural Science Foundation of China(22207063),111 Project(D20015)the Natural Science Research Project of Yichang City(A23-2-002)the Opening Funding of Hubei Key Laboratory of Natural Products Research and Development,China Three Gorges University(2024NPRD03,2024NPRD04,2024NPRD05).
文摘Vicinal all-carbon quaternary stereocenters are widely present in natural products and bioactive molecules.However,the construction of such motif in one step from readily available starting materials remains a significant challenge.Herein,we report a phosphine-catalyzed divergent γ,γ-and ε,γ-umpolung domino addition of bisoxindoles with allenoates.This method serves as a practical tool for the concise synthesis of a series of bisoxindole derivatives bearing sterically hindered vicinal all-carbon quaternary stereocenters under mild reaction conditions.The applicability of this novel method was demonstrated with the gram-scale synthesis of three known advanced intermediates for the total syntheses of calycanthine,chimonanthine and folicanthine.
