Direct Arylation of Juglone Enables Divergent Access to WS-5995 Analogs
Related Experiment Video
Updated: Oct 30, 2026

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
Published on: July 6, 2016
Yusuke Akagi1, Yoshimi Shimizu1,2, Erika Iwasaki1
1Faculty of Pharmaceutical Sciences, Teikyo Heisei University, 4-21-2 Nakano, Nakano-ku, Tokyo 164-8530, Japan.
Abstract:
The direct arylation of juglone enables concise access to WS-5995A and the related natural product WS-5995C, providing an entry to the WS-5995 family. The method affords access to lactam analogs via either C-2 or C-3 arylation, enabling the variation of the phenolic hydroxyl position. Cytotoxicity studies reveal a pronounced effect of the phenolic hydroxyl group positioning on biological activity, with the C-3-derived lactam showing enhanced potency. Further demethylation of WS-5995A increases activity, suggesting an important role of a free phenolic hydroxyl group.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Stereoisomerism of Cyclic Compounds
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

