Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 29, Pages 9025-9029Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03712
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Funding
- National Natural Science Foundation of China [21525209, 21621002, 21772225, 21761142003]
- Chinese Academy of Sciences (Strategic Priority Research Program) [XDB20000000]
- Chinese Academy of Sciences (Key Research Program of Frontier Sciences) [QYZDB-SSW-SLH040]
- Shanghai Science and Technology Commission [15JC1400400, 17XD1404600]
- National Program for Support of Top-Notch Young Professionals of China
- K. C. Wong Education Foundation
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Septedine (2) is a hetidine type C-20-diterpenoid alkaloid bearing an oxygenated heptacyclic scaffold. We have accomplished the first and asymmetric total synthesis of 2 and its 7-deoxy analogue 3. A functionalized tricyclic intermediate was prepared with excellent enantiopurity by using Carreira polyene cyclization. An unusual anionic Diels-Alder reaction was responsible for the construction of the bicyclo[2.2.2]-octane. The alpha-methyl ketone was furnished by iridium catalyzed allylic alcohol isomerization. Sanford Csp(3)-H oxidation was exploited to install the secondary hydroxy group of 2. The oxazolidinopiperidine was assembled by selective reductive amination and spontaneous N,O-ketalization at a final stage.
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