Silver-catalyzed one-pot synthesis of arylnaphthalene lactones.
Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied.
Eghbali
Nicolas
N
Center for Green Chemistry and Green Engineering at Yale, Yale Chemistry Department, 225 Prospect Street, New Haven, Connecticut 06520, USA.
Eddy
Jennifer
J
Anastas
Paul T
PT
D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D002245:Carbon Dioxide / Q000737:chemistry; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D017705:Lignans / Q000737:chemistry*; D008956:Models, Chemical; D009281:Naphthalenes / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*
D000480:Alkynes; D001688:Biological Products; D002934:Cinnamates; D006842:Hydrocarbons, Brominated; D007783:Lactones; D017705:Lignans; D009281:Naphthalenes; D002245:Carbon Dioxide; C031721:naphthalene; C044736:phenylacetylene; D012834:Silver; D000114:Acetylene