Annulation strategies for benzo[b]fluorene synthesis: efficient routes to the kinafluorenone and WS-5995 antibiotics.

Bioorganic and Medicinal Chemistry Laboratories, Department of Chemistry, Northeastern University, 360 Huntington Avenue, Boston, Massachussetts 02115-5000, USA.

The Journal of organic chemistry 2000 Oct 20

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Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative to Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.

Citation

G Qabaja, G B Jones. Annulation strategies for benzo[b]fluorene synthesis: efficient routes to the kinafluorenone and WS-5995 antibiotics. The Journal of organic chemistry. 2000 Oct 20;65(21):7187-94