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Total Synthesis of Spiroalkaloids Lycibarbarines A–C |
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| Authors: | Pengpeng Nie Chuanfang Zhao Shuai Yu Dr Jun Liu Dr Yuguo Du |
| Institution: | 1. State Key Laboratory of Environmental, Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing, 100085 P. R. China
School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China;2. State Key Laboratory of Environmental, Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing, 100085 P. R. China |
| Abstract: | The concise and efficient synthesis of tetrahydroquinoline alkaloids lycibarbarines A−C has been accomplished in four steps from a common intermediate derived from commercially available 2-deoxy-D-ribose and 8-hydroxyquinoline. For the synthesis of the unique tetracyclic spiro-heterocycle skeleton we employed a synthetic strategy that features two key transformations: iodomethyllithium-based homologation of lactone / N-alkylation to access tetracyclic spiro-heterocycle skeleton in one step and one-pot acetonide deprotection, hemiacetal formation, and spirocyclization cascade process. |
| Keywords: | alkaloids lycibarbarines A−C spiroketal tetrahydroquinoline total synthesis |