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Synthesis of Aza ‐Rocaglates via ESIPT‐Mediated (3+2) Photocycloaddition
Author(s) -
Wang Wenyu,
Cencic Regina,
Whitesell Luke,
Pelletier Jerry,
Porco John A.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602953
Subject(s) - chemistry , stereochemistry , medicinal chemistry
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.