Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 17, Pages 6098-6101Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b02746
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Funding
- Zhejiang Natural Science Fund for Distinguished Young Scholars [LR16B020001]
- National Natural Science Foundation of China [21622205, 21472167]
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The unprecedented oxidative dearomatization-induced [5+2] cycloaddition/pinacol-type 1,2-acyl migration cascade efficiently generates a quaternary carbon center and assembles the highly oxygenated bicyclo[3.2.1]octane framework of ent-kaurene diterpenoids. By incorporation of the subsequent retro-aldol/aldol process and singlet oxygen ene reaction, this concise and convergent approach has enabled the first asymmetric total syntheses of pharicin A, pharicinin B, 7-O-acetylpseurata C, and pseurata C.
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