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Asymmetric approach towards the total synthesis of (+)-actinopyllic acid |
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| Authors: | Fei Xue Tao Xiao Min Li Kai-Fang Zhang Li-Ping He Yong Qin Xiao-Yu Liu Dan Zhang |
| Affiliation: | 1. Innovative Drug Research Centre (IDRC), School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China;2. Key Laboratory of Drug Targeting and Novel Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China |
| Abstract: | This paper describes our efforts towards the asymmetric total synthesis of (+)-actinophyllic acid. Starting from the chiral oxazolidinone 9, an azocino [4,3-b]indolyl intermediate (5) possessing the A/B/C ring system and the C16 quaternary stereogenic center of actinophyllic acid has been synthesized. Key steps include a LHMDS-promoted condensation to establish the critical C2–C16 bond and a successive four-step transformation to assemble the eight-membered C-ring of the target molecule. |
| Keywords: | Actinopyllic acid Asymmetric synthesis Indole synthesis Chiral oxazolidinone Corresponding author. |
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