Asymmetric Synthesis of Arboduridine-Reference-Cited by-同舟云学术

Asymmetric Synthesis of Arboduridine

Published:2023-12-15 Issue:3 Volume:63 Page:
ISSN:1433-7851
Container-title:Angewandte Chemie International Edition
language:en
Short-container-title:Angew Chem Int Ed

Author:

Yang Rui¹,Zhou Zeyu¹,Jiang Huanfeng¹,Kam Toh‐Seok²,Chen Kai³,Ma Zhiqiang¹⁴^ORCID

Affiliation:

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

4. State Key Laboratory of Chemical Oncogenomics Guangdong Provincial Key Laboratory of Chemical Genomics Peking University Shenzhen Graduate School Shenzhen Guangdong 518055 P.R. China

Abstract

AbstractThe 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.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202316016

Reference102 articles.

1. For selected reviews on isolation bioactivities or synthesis ofKopsiaindole alkaloids see:

2. “Alkaloids ofKopsia”: T.-S. Kam K.-H. Lim inThe Alkaloids:Chemistry and Biology Vol. 66(Ed.: G. A. Cordell) Academic Press San Diego 2008 pp. 1–111;

3. Total synthesis of kopsine, fruticosine, and structurally related polycyclic caged Kopsia indole alkaloids

4. Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

5. A comprehensive review on phytochemistry and pharmacology of genus Kopsia: monoterpene alkaloids – major secondary metabolites

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Total Synthesis of (+)-Arboduridine;Synfacts;2024-02-14