Catalytic Asymmetric Construction of α‐Quaternary Cyclopentanones and Its Application to the Syntheses of (−)‐1,14‐Herbertenediol and (−)‐Aphanorphine |
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| Authors: | Dao‐Yong Zhu Ming‐Hui Xu Prof?Dr Yong‐Qiang Tu Prof?Dr Fu‐Min Zhang Prof?Dr Shao‐Hua Wang |
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| Institution: | 1. State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.?R. China), Fax: (+86)?931‐8912582;2. School of Pharmacy, Lanzhou University, and Key Laboratory of Drug, Targeting and Drug Delivery System, Ministry of Education, Sichuan University, Chengdu (P.?R. China) |
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| Abstract: | A novel and efficient strategy to build α‐benzylic quaternary cyclopentanones with excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 % yield) has been developed, and its application demonstrated by the first catalytic asymmetric total synthesis of (?)‐1,14‐herbertenediol and the formal synthesis of (?)‐aphanorphine. |
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| Keywords: | asymmetric synthesis enantioselectivity organocatalysis quaternary stereocenters sesquiterpenes |
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