Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones.
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.
Cong
Huan
H
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Becker
Clinton F
CF
Elliott
Sean J
SJ
Grinstaff
Mark W
MW
Porco
John A
JA
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*
D000970:Antineoplastic Agents; D001688:Biological Products; D047188:Chalcones; C482884:panduratin A; D012834:Silver; D012822:Silicon Dioxide; C013031:2'-hydroxychalcone