期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 51, 页码 20048-20052出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12034
关键词
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资金
- College of Chemistry and Molecular Engineering, Peking University
- Peking-Tsinghua Center for Life Sciences
- Beijing National Laboratory for Molecular Sciences
- National Science Foundation of China [31521004, 21672011, 21822101]
- National Key Research and Development Program of China [2017YFA0104003]
- PKUAIC
- High-Performance Computing Platform of Peking University
An enantioselective total synthesis of (-)-oridonin is accomplished based on a key interrupted Nazarov reaction. The stereochemistry of the Nazarov/Hosomi-Sakurai cascade was first explored to forge a tetracyclic skeleton with challenging quaternary carbons. A delicate sequence of two ring-rearrangements and late stage redox manipulations was carried out to achieve the de novo synthesis of this highly oxidized ent-kauranoid.
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