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Asymmetric Total Synthesis of Propindilactone G,Part 1: Initial Attempts towards the Synthesis of Schiartanes |
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| Authors: | Dr. Ling‐Ming Xu Dr. Lin You Dr. Zhen‐Hua Shan Ruo‐Cheng Yu Bo Zhang Yuan‐He Li Ying Shi Prof. Dr. Jia‐Hua Chen Prof. Dr. Zhen Yang |
| Affiliation: | 1. State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, Beijing, P.?R. China;2. +86)?10‐6275‐9105;3. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, P.?R. China;4. Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P.?R. China |
| Abstract: | Our first‐generation synthetic study towards the total synthesis of propindilactone G ( 1 ) and its analogues is reported. The key synthetic steps were an intramolecular Pauson–Khand reaction (PKR) and a vinylogous Mukaiyama reaction (VMAR). The stereoselective synthesis of the CDE ring moiety with an all‐carbon quaternary center through a PKR was difficult, whilst a VMAR afforded a product with the opposite stereochemistry at the C20 position on the side chain. These results led us to redesign our synthetic strategy for the total synthesis of compound 1 . |
| Keywords: | natural products nortriterpenoids propindilactone G synthetic methods total synthesis |