title: Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis.
abstract: An efficient method for the asymmetric Diels-Alder cycloaddition of 2'-hydroxychalcones with acyclic or cyclic dienes has been successfully developed. The Diels-Alder cycloaddition is mediated by a chiral boron complex with VANOL, affording the corresponding products in high yields and with excellent diastereo- and enantioselectivities. This reaction enabled the enantioselective construction of cyclohexene skeletons crucial for the total synthesis of a number of Diels-Alder-type natural products (-)-nicolaioidesin C, (-)-panduratine A, (-)-kuwanon I, (+)-kuwanon J, and (-)-brosimones A and B.
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, China.|National Institute of Biological Sciences (NIBS) , Beijing, 102206, China.
authors.forename: Xia
authors.initials: X
authors.lastname: Li
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, China.|National Institute of Biological Sciences (NIBS) , Beijing, 102206, China.
authors.forename: Jianguang
authors.initials: J
authors.lastname: Han
authors.affiliation: 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 Center for Life Sciences, Peking University , Beijing, 100871, China.
authors.forename: Alexander X
authors.initials: AX
authors.lastname: Jones
authors.affiliation: 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 Center for Life Sciences, Peking University , Beijing, 100871, China.
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Lei
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D047188:Chalcones / Q000737:chemistry*; D061565:Cycloaddition Reaction; D053138:Cyclohexenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D001896:Boron Compounds; D047188:Chalcones; D053138:Cyclohexenes; C052568:cyclohexene; C013031:2'-hydroxychalcone