Wang, Cheng and Pang, Yubing and Wu, Yuecheng and Zhang, Nanping and Yang, Rui and Li, Ying and Chen, Pengquan and Jiang, Huanfeng and Xu, Xue-Tao and Kam, Toh-Seok and Fan, Ting and Ma, Zhiqiang (2021) Divergent synthesis of skeletally distinct arboridinine and arborisidine. Angewandte Chemie International Edition, 60 (52). pp. 26978-26985. ISSN 1433-7851, DOI https://doi.org/10.1002/anie.202110149.
Full text not available from this repository.Abstract
A divergent synthesis of skeletally distinct arboridinine and arborisidine was achieved. The central divergent strategy was inspired by the divergent biosynthetic cyclization mode of arboridinine and arborisidine and their hidden topological connection. The branch point was reached through a Michael and Mannich cascade process. A site-selective intramolecular Mannich reaction was developed to construct the tetracyclic core of arboridinine, while a site-selective intramolecular alpha-amination of ketone was used to access the tetracyclic core of arborisidine. A strategic Peterson olefination through intramolecular nucleophile delivery was able to set up the exocyclic olefin of arboridinine.
| Item Type: | Article |
|---|---|
| Funders: | National Natural Science Foundation of China (NSFC) [Grant No: 21871098 & 22071064 & 21672073 & 21803019], National Program on Key Research Project [Grant No: 2016YFA0602900], National Natural Science Foundation of Guangdong Province [Grant No: 2017B090903003], Youth Science and Technology Talent Promotion Fund [Grant No: X20200301056], Science and Technology Program of Guangzhou [Grant No: 201707010073], Fundamental Research Funds for the Central Universities, SCUT, China Postdoctoral Science Foundation [Grant No: 2018M643063] |
| Uncontrolled Keywords: | Alkaloids; Arboridinine; Arborisidine; Divergent synthesis; Total synthesis |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms Zaharah Ramly |
| Date Deposited: | 30 May 2022 01:50 |
| Last Modified: | 30 May 2022 01:50 |
| URI: | http://eprints.um.edu.my/id/eprint/34576 |
Actions (login required)
 |
View Item |
