Asymmetric synthesis of arboduridine

Yang, Rui and Zhou, Zeyu and Jiang, Huanfeng and Kam, Toh Seok and Chen, Kai and Ma, Zhiqiang (2024) Asymmetric synthesis of arboduridine. Angewandte Chemie - International Edition, 63 (3). ISSN 1433-7851, DOI

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The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been accomplished. The tricyclic A/B/D ring system was constructed by an enantioselective Michael reaction followed by intramolecular nucleophilic addition. Intramolecular α-amination of a ketone forged the piperidine ring, while a Horner–Wadsworth–Emmons (HWE) reaction was used to form the pyrrolidine ring. A reduction cyclization cascade led to formation of the tetrahydrofuran ring. © 2023 Wiley-VCH GmbH.

Item Type: Article
Funders: National Natural Science Foundation of China [Grant no. 21871098, 22003077, 22071064, 22271099], South China University of Technology, National Key Research and Development Program of China [Grant no. 2016YFA0602900]
Uncontrolled Keywords: Asymmetric catalysis; Michael addition; Monoterpenoid indole alkaloids; Total synthesis
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 25 Apr 2024 01:40
Last Modified: 25 Apr 2024 01:40

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