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Total Synthesis of the Diterpenoid (+)‐Harringtonolide |
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| Authors: | Dr. Zhiqiang Ma Dr. Ruining Li Zhen Zhang Cheng Tao Dr. Bin Cheng Dr. Yun Li Dr. Huifei Wang Prof. Dr. Hongbin Zhai |
| Affiliation: | 1. CAS-Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China;2. The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, China;3. Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen, China;4. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, Tianjin, China |
| Abstract: | Described herein is the first asymmetric total synthesis of (+)‐harringtonolide, a natural diterpenoid with an unusual tropone imbedded in a cagelike framework. The key transformations include an intramolecular Diels–Alder reaction and a rhodium‐complex‐catalyzed intramolecular [3+2] cycloaddition to install the tetracyclic core as well as a highly efficient tropone formation. |
| Keywords: | asymmetric synthesis cycloaddition natural products terpenoids total synthesis |