Asymmetric Synthesis of Arboduridine

Yang R 1 , Zhou Z 1 , Jiang H 1 , Kam TS 2 , Chen K 3 , Ma Z 1

Affiliations 

  • 1 Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China
  • 2 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia
  • 3 College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, P. R. China
Angew Chem Int Ed Engl, 2024 Jan 15;63(3):e202316016.
PMID: 38038685 DOI: 10.1002/anie.202316016

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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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