Asymmetric synthesis of arboduridine

Authors

• Rui Yang
• Zeyu Zhou
• Huanfeng Jiang
• Toh Seok KamFollow
• Kai Chen
• Zhiqiang Ma

Document Type

Article

Publication Date

1-1-2024

Abstract

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.

Keywords

Asymmetric catalysis, Michael addition, Monoterpenoid indole alkaloids, Total synthesis

Publication Title

Angewandte Chemie - International Edition

Recommended Citation

Yang, Rui; Zhou, Zeyu; Jiang, Huanfeng; Kam, Toh Seok; Chen, Kai; and Ma, Zhiqiang, "Asymmetric synthesis of arboduridine" (2024). Research Publications (2021 to 2025). 3835.
https://knova.um.edu.my/research_publications_2021_2025/3835

Divisions

CHEMISTRY

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]

Volume

63

Issue

3

Publisher

John Wiley and Sons Inc