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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.

SUBMITTER: Wang W

PROVIDER: S-EPMC5224829 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.

Wang Wenyu W Cencic Regina R Whitesell Luke L Pelletier Jerry J Porco John A JA

Chemistry (Weinheim an der Bergstrasse, Germany) 20160715 34

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. ...[more]

PMID: 27338157

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