Synthetic study toward the total synthesis of maoecrystal V.
A novel and concise approach for the construction of the core structure of maoecrystal V (1) has been developed. Utilizing the lead-mediated arylation of beta-ketoesters and oxidative dearomatization/IMDA reaction as key steps, the two consecutive all-carbon quaternary centers (C-9 and C-10) were constructed in a stereoselective manner. The developed chemistry paves the way for the total synthesis of this fascinating natural product.
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China.
Jianxian
J
Gong
Guang
G
Lin
Chuang-chuang
CC
Li
Zhen
Z
Yang
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D037602:Isodon / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D004224:Diterpenes; D004365:Drugs, Chinese Herbal; C473434:maoecrystal A