“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.