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Asymmetric Total Synthesis of (-)-Maoecrystal V
Wei-bin Zhang1, Wen-bin Shao1, Fu-zhuo Li1
1Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
Abstract:
The asymmetric total synthesis of (-)-maoecrystal V, a novel cytotoxic pentacyclic ent-kaurane diterpene, has been accomplished. Key steps of the current strategy involve an early-stage semipinacol rearrangement reaction for the construction of the C10 quaternary stereocenter, a rhodium-catalyzed intramolecular O-H insertion reaction, and a sequential Wessely oxidative dearomatization/intramolecular Diels-Alder reaction to forge the pentacyclic framework of maoecrystal V.
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