Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel-Mediated Cyclization of Tryptamine-Ynamide
Changhong Han
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
These authors contributed equally to this work.
Search for more papers by this authorLu Yang
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
These authors contributed equally to this work.
Search for more papers by this authorKaizong Yao
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorSen Zhang
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorJiayue Fu
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorHanyang Sun
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorHongsheng Xu
Zhejiang Shapuaisi Pharmaceutical Co., Ltd., Pinghu, Zhejiang, 314299 China
Search for more papers by this authorBin Lin
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorMaosheng Cheng
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorCorresponding Author
Yongxiang Liu
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
E-mail: [email protected]Search for more papers by this authorChanghong Han
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
These authors contributed equally to this work.
Search for more papers by this authorLu Yang
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
These authors contributed equally to this work.
Search for more papers by this authorKaizong Yao
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorSen Zhang
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorJiayue Fu
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorHanyang Sun
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorHongsheng Xu
Zhejiang Shapuaisi Pharmaceutical Co., Ltd., Pinghu, Zhejiang, 314299 China
Search for more papers by this authorBin Lin
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorMaosheng Cheng
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
Search for more papers by this authorCorresponding Author
Yongxiang Liu
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016 China
Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning, 117000 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
An asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps (8 purifications) from L-tryptophan. The main feature of our synthetic strategy is the efficient construction of spirocyclic oxindole intermediate containing a chiral quaternary carbon center, involving the silica gel-mediated cyclization of tryptamine-ynamide and oxidation under neat conditions.
Supporting Information
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Appendix S1: Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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