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Peer-reviewedCC BY-NCChemical and Pharmaceutical Bulletin

Direct Arylation of Juglone Enables Divergent Access to WS-5995 Analogs

  • Yusuke Akagi
  • Yoshimi Shimizu
  • Erika Iwasaki
  • Yuichiro Taira
  • Toshiya Komatsu
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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.

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Cite

BibTeXRIS
BibTeX
@article{akagi2026direct,
  title = {{Direct Arylation of Juglone Enables Divergent Access to WS-5995 Analogs}},
  author = {Yusuke Akagi and Yoshimi Shimizu and Erika Iwasaki and Yuichiro Taira and Toshiya Komatsu},
  journal = {Chemical and Pharmaceutical Bulletin},
  year = {2026},
  month = oct,
  doi = {10.1248/cpb.c26-00475},
  url = {https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00475/_article},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Direct Arylation of Juglone Enables Divergent Access to WS-5995 Analogs
AU  - Yusuke Akagi
AU  - Yoshimi Shimizu
AU  - Erika Iwasaki
AU  - Yuichiro Taira
AU  - Toshiya Komatsu
PY  - 2026
DA  - 2026/10/27
JO  - Chemical and Pharmaceutical Bulletin
DO  - 10.1248/cpb.c26-00475
UR  - https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00475/_article
AB  - 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.
SN  - 1347-5223
SN  - 0009-2363
ER  -