A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes
A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)<sub>3</sub> as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.
Authors
- Peng-Juan Li
- Yong Tang (ORCID: https://orcid.org/0000-0002-5435-9938)
- Xiao‐Kang Kuang
- Lijia Wang (ORCID: https://orcid.org/0000-0002-6657-3392)
- Jun Zhu (ORCID: https://orcid.org/0009-0005-6817-3068)
Institutions
- Chinese Academy of Sciences (CN)
- Southern University of Science and Technology (CN)
- Shanghai Institute of Organic Chemistry (CN)
- East China Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-30
- DOI
- https://doi.org/10.1021/acs.joc.4c02509
- Citations
- 2
- Primary Topic
- Alkaloids: synthesis and pharmacology
- Type
- article
- Field-Weighted Citation Impact
- 0.93
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities