Construction of the Lactone-Bridged Scaffold of Alstoscholactine through an Acid-Catalyzed Prins Cyclization/Lactonization Cascade
Described herein is an acid-catalyzed Prins cyclization/lactonization cascade reaction of malonate-tethered inol-3-ylmethanol-olefin substrates, which rapidly constructs the lactone-bridged scaffold of the monoterpenene indole alkaloid alstoscholactine. This reaction demonstrates a wide substrate scope and functional group tolerance, and a catalytic asymmetric reaction provides high enantioselectivity. This work provides a powerful method to access the key framework of alstoscholactine and supports the proposed plausible biogenetic pathway.
Authors
- Bowen Fang
- Zhi Zhen Qin (ORCID: https://orcid.org/0000-0002-3956-5223)
- Zhiyu Zhang (ORCID: https://orcid.org/0000-0002-8594-9770)
- Huilin Li (ORCID: https://orcid.org/0000-0001-8088-6718)
- Xinyu Liang (ORCID: https://orcid.org/0000-0003-0964-4294)
- Yuting Yang (ORCID: https://orcid.org/0009-0007-5922-0509)
- Y. Y. Duan (ORCID: https://orcid.org/0000-0003-2469-9111)
- Xuegong She (ORCID: https://orcid.org/0000-0002-3002-2433)
Institutions
- Minzu University of China (CN)
- Guizhou University (CN)
- State Ethnic Affairs Commission (CN)
- Shanghai Pesticide Research Institute (CN)
- State Key Laboratory of Chemical Engineering (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c02725
- Citations
- 1
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Guizhou University
- Fundamental Research Funds for the Central Universities
- Science and Technology Program of Gansu Province