lignans and phenylacetylene

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.

Topics: Acetylene; Alkynes; Biological Products; Carbon Dioxide; Catalysis; Cinnamates; Cyclization; Hydrocarbons, Brominated; Lactones; Lignans; Models, Chemical; Naphthalenes; Silver