Total Synthesis and Stereochemical Assignment of Actinoranone.
The total synthesis of four actinoranone stereoisomers led to unambiguous assignment of relative and absolute stereochemistry of the natural product. Key features of the convergent, fully stereocontrolled route include the use of a Negishi carbozirconation/iodination, a Friedel-Crafts cyclization, a Felkin-controlled addition reaction, a Mitsunobu reaction, and a late-stage C-H oxidation.
Key Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055, China.
Yi-An
YA
Guo
Key Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055, China.
Meng
M
Zhao
Key Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055, China.
Zhengshuang
Z
Xu
Key Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055, China.
Tao
http://orcid.org/0000-0002-2780-9761
T
Ye
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
D001688:Biological Products; D004224:Diterpenes; C587941:actinoranone; D015040:Zirconium
actinoranone; meroterpenoid; natural products; stereochemistry; total synthesis