Asymmetric synthesis of arboduridine
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
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]
Publication Title
Angewandte Chemie - International Edition
Volume
63
Issue
3
Publisher
John Wiley and Sons Inc