title: Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones.
abstract: Metal nanoparticles are currently being employed as catalysts for a number of classical chemical transformations. In contrast, identification of novel reactions of nanoparticles, especially toward the synthesis of complex natural products and derivatives, is highly underdeveloped and represents a bourgeoning area in chemical synthesis. Herein, we report silica-supported silver nanoparticles as solid, recyclable catalysts for Diels-Alder cycloadditions of 2'-hydroxychalcones and dienes in high yield and turnover number. The use of silver nanoparticle catalysts is further demonstrated by the total synthesis of the cytotoxic natural product panduratin A employing a highly electron-rich dienophile and Lewis acid sensitive diene.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
authors.forename: Huan
authors.initials: H
authors.lastname: Cong
authors.forename: Clinton F
authors.initials: CF
authors.lastname: Becker
authors.forename: Sean J
authors.initials: SJ
authors.lastname: Elliott
authors.forename: Mark W
authors.initials: MW
authors.lastname: Grinstaff
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D053768:Metal Nanoparticles / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D012834:Silver / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D047188:Chalcones; C482884:panduratin A; D012834:Silver; D012822:Silicon Dioxide; C013031:2'-hydroxychalcone