title: Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.
abstract: 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.
authors.affiliation: Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, MA, 02215, USA.
authors.forename: Wenyu
authors.initials: W
authors.lastname: Wang
authors.affiliation: Department of Biochemistry and The Rosalind and Morris Goodman Cancer Research Centre Room 810, McGill University, 3655 Drummond St., Montreal, QC, H3G 1Y6, Canada.
authors.forename: Regina
authors.initials: R
authors.lastname: Cencic
authors.affiliation: Whitehead Institute for Biomedical Research (WIBR), Cambridge, MA, 02142, USA.
authors.forename: Luke
authors.initials: L
authors.lastname: Whitesell
authors.affiliation: Department of Biochemistry and The Rosalind and Morris Goodman Cancer Research Centre Room 810, McGill University, 3655 Drummond St., Montreal, QC, H3G 1Y6, Canada.
authors.forename: Jerry
authors.initials: J
authors.lastname: Pelletier
authors.affiliation: Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, MA, 02215, USA. porco@bu.edu.
authors.forename: John A
authors.identifier: http://orcid.org/0000-0002-2991-5680
authors.initials: JA
authors.lastname: Porco
keywords: ESIPT; flow chemistry; heterocycles; photocycloaddition; rocaglate