Asymmetric synthesis of isoquinoline alkaloids |
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| Institution: | 1. Key Laboratory of Marine Drugs Chinese Ministry of Education/ Sanya Oceanographic Institute, Ocean University of China, Qingdao 266003/Sanya 572025, China;2. Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China;3. Marine Biomedical Research Institute of Qingdao, Ocean University of China, Qingdao 266071, China |
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| Abstract: | The use of chiral formamidines affixed to variously substituted tetrahydroisoquinolines, allows asymmetric C-C bond forming reactions to occur α- to the amino group. In this manner, a wide variety of (S)-1-alkyl-1,2,3,4-tetrahydroisoquinolines were constructed in > 90% enantiomeric excess. Choosing the proper substituents and skeletal features, an efficient entry into the benzylisoquinoline, tetrahydroprotoberberine, aporphine, and isopavine class of alkaloids was achieved. |
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