Total Synthesis of Vinigrol†
Qingliang Yang
Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)
Search for more papers by this authorCorresponding Author
Prof. Jon T. Njardarson
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)Search for more papers by this authorDr. Cristian Draghici
Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)
Search for more papers by this authorDr. Fang Li
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
Search for more papers by this authorQingliang Yang
Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)
Search for more papers by this authorCorresponding Author
Prof. Jon T. Njardarson
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)Search for more papers by this authorDr. Cristian Draghici
Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)
Search for more papers by this authorDr. Fang Li
Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
Search for more papers by this authorWe thank the NIH-NIGMS (RO1 GM086584) for generous financial support of this program.
Graphical Abstract
Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels–Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.
Supporting Information
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