Unified total synthesis of eburnamine-vincamine indole alkaloids based on catalytic asymmetric hydrogenation/lactamization cascade  

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作  者:Wen Zhang Yansong Xue Srihari Konduri Guodan Lin Mengjuan Wu Pei Tang Fener Chen 

机构地区:[1]Sichuan Research Center for Drug Precision Industrial Technology,West China School of Pharmacy,Sichuan University,Chengdu 610041,China [2]Engineering Center of Catalysis and Synthesis for Chiral Molecules,Department of Chemistry,Fudan University,Shanghai 200433,China [3]Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs,Shanghai 200433,China [4]Skaggs School of Pharmacy and Pharmaceutical Science,UC San Diego,9500 Gilman Drive,La Jolla,CA 92093-0934,United States

出  处:《Green Synthesis and Catalysis》2022年第3期291-293,共3页绿色合成与催化(英文)

基  金:support from the National Natural Science Foundation of China(No.U21A20278);the Sichuan Science and Technology Program(No.2021YJ0221).

摘  要:The enantioselective total synthesis of representative members of the eburnamine-vincamine alkaloids(+)-vincamine,(-)-eburnamonine,and(-)-criocerine has been accomplished.The synthesis took advantage of a highly stereoselective Ir-catalyzed hydrogenation/lactamization cascade reaction,which allows for the stereo-selective construction of the C/D rings as well as the installation of the critical cis-C20/C21 relative stereo-chemistry of the eburnamine-vincamine alkaloid skeleton in one pot.

关 键 词:Indole alkaloid IMINE Asymmetric hydrogenation Natural product Enantioselective synthesis 

分 类 号:O62[理学—有机化学]

 

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