Synthesis of 7-Epi +-FR900482: an epimer of comparable anti-cancer activity.

Abstract

FR900482 is a potent anti-tumor therapeutic that has been investigated as a replacement candidate for the clinically useful Mitomycin C. Herein, we report synthesis and biological testing of 7-Epi (+)-FR900482, which demonstrates equal potency relative to the natural product against several cancer cell lines. Highlights of this work include utilization of our palladium-catalyzed DYKAT methodology and development of a Polonovski oxidative ring expansion strategy to yield this equipotent epimer in 23 linear steps.

• Authors: Barry M Trost, Brendan M O'Boyle
• Journal: Organic letters (Org Lett) Vol. 10 Issue 7 Pg. 1369-72 (Apr 03 2008) ISSN: 1523-7060 [Print] United States
• PMID: 18318539 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• 7-epi-FR900482
• Antineoplastic Agents
• Oxazines
• FR 900482

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Molecular Structure
• Oxazines (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism