title: Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A.
abstract: The first enantioselective total syntheses of (-)-kuwanon X, (+)-kuwanon Y, and (+)-kuwanol A have been accomplished by using asymmetric Diels-Alder cycloaddition promoted by chiral VANOL or VAPOL/boron Lewis acid. The biosynthesis-inspired asymmetric Diels-Alder cycloaddition shows high exo selectivity (exo/endo = 13/1), which was unprecedented in the previous total syntheses of related prenylflavonoid Diels-Alder natural products. An acid catalyzed intramolecular ketalization process enabled a biomimetic transformation to construct the polycyclic skeleton of kuwanol A efficiently.
authors.affiliation: Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100730, China.|National Institute of Biological Sciences (NIBS) , Beijing 102206, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Gao
authors.affiliation: National Institute of Biological Sciences (NIBS) , Beijing 102206, China.
authors.forename: Jianguang
authors.initials: J
authors.lastname: Han
authors.affiliation: Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100730, China.|National Institute of Biological Sciences (NIBS) , Beijing 102206, China.|Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking-Tsinghua Center for Life Sciences, Peking University , Beijing 100871, China.
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Lei
mesh_terms: D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005419:Flavonoids; D058116:Lewis Acids; C000608190:kuwanol A; C000608187:kuwanon X; C000608189:kuwanon Y