Stereoselective Synthesis of the Core Ring System of Lancifonins A–D
A 5/5/7 tricyclic intermediate bearing an oxa-bridged hemiketal ring was successfully synthesized from dihydrocarvone in 14 steps, which is a common intermediate of various <i>Schisandra</i> nortriterpenoids. Subsequently, the core structure of lancifonins A-D, characterized by a 5/5/7/8 fused ring system, was constructed in seven steps. The route employs key transformations, including the aldol reaction, Mukaiyama hydration, Mn(III)-mediated cyclization, the Suzuki reaction, and McMurry coupling.
Authors
- Jie-Lun Yan (ORCID: https://orcid.org/0000-0003-3340-2746)
- Pingping Tang (ORCID: https://orcid.org/0000-0002-8296-5695)
- Tengying Chen
- Mingxin Zhao (ORCID: https://orcid.org/0000-0001-5148-4218)
- Lu Guo (ORCID: https://orcid.org/0000-0003-4369-2513)
- Haowen Tian (ORCID: https://orcid.org/0000-0003-1882-2072)
- Kaishun Bi (ORCID: https://orcid.org/0000-0002-8622-267X)
- Qingyun Huang
Institutions
- Nankai University (CN)
- Institute of Organic Chemistry (HU)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00263
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Tianjin City
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities