“Chemical Synthesis and Biological Studies of the Rocaglates and Derivatives”

The plant genus Aglaia produces a number of secondary metabolites including the

cyclopenta[b]benzofuran silvestrol. Cyclopenta[b]benzofuran natural products possess 

potent anticancer properties due to modulation of the activity of the RNA helicase 

eukaryotic initiation factor 4A (eIF4A), which is involved in loading ribosomes onto 

mRNA templates during translation initiation, a step frequently deregulated in cancer. In 

this presentation, we will describe our efforts to synthesize silvestrol and rocaglate 

analogues using photocycloaddition of 3-hydroxyflavones with various dipolarophiles, 

and evaluation of the rocaglates produced as inhibitors of eukaryotic protein translation.

Originally published at chemistry.nd.edu.