Synthesis of aza-rocaglates via ESIPT-mediated (3+2) photocycloaddition
Porco, John A.
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Citation (published version)Wenyu Wang, Regina Cencic, Luke Whitesell, Jerry Pelletier, John A Porco. 2016. "Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.." Chemistry, Volume 22, Issue 34, pp. 12006 - 12010.
Synthesis of aza-rocaglates, nitrogen-containing analogues of the rocaglate natural products, is reported. The route features ESIPT-mediated (3+2) photocycloaddition of 1-alkyl-2-aryl-3-hydroxyquinolinones with the dipolarophile methyl cinnamate. A continuous photoflow reactor was utilized for photocycloadditions. An array of compounds bearing the hexahydrocyclopenta[b]indole core structure was synthesized and evaluated in translation inhibition assays.