Enantioselective Total Syntheses of (+)-Kobusine, (+)-Spirasine IX and the Purported Structure of (+)-Orgetine: Strategic Use of C–H Bonds
Enantioselective total syntheses of (+)-kobusine, (+)-spirasine IX and the proposed structure of (+)-orgetine were achieved. A unique approach was developed to construct a cage-like hexacyclic ring system that underwent an HAT-initiated radical rearrangement to forge the hetisine-type scaffold. Subsequent late-stage redox manipulations, including an intramolecular hydride shift, were deployed to provide different C20-diterpenoid alkaloids.
Authors
- Tuoping Luo (ORCID: https://orcid.org/0000-0003-2156-3198)
- Fanrui Wu (ORCID: https://orcid.org/0000-0002-6347-2131)
- Mengping Deng
- Tongfeng Liu
- Zhe Jiang (ORCID: https://orcid.org/0000-0003-2454-1103)
Institutions
- Peking University (CN)
- Shenzhen Bay Laboratory (CN)
- Institute of Molecular Medicine (IN)
- Center for Life Sciences (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/jacs.5c00650
- Citations
- 8
- Primary Topic
- Plant-based Medicinal Research
- Type
- article
- Field-Weighted Citation Impact
- 12.46
Funders
- National Natural Science Foundation of China
- Shenzhen Bay Laboratory
- Beijing National Laboratory for Molecular Sciences