Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 16, Pages 4818-4822Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411663
Keywords
anodic oxidation; electrosynthesis; macrocycles; natural products; oxazoles
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Funding
- Diazon Pharma
- NSF [CHE-1048804]
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An electrochemical method to synthesize the core macrolactam of diazonamides is described. Large ring-forming dehydrogenation is initiated by anodic oxidation at a graphite surface. The reaction requires no tailoring of the substrate and occurs at ambient temperature in aqueous DMF in an undivided cell open to air. This unique chemistry has enabled a concise, scalable preparation of DZ-2384; a refined analog of diazonamide A slated for clinical development as a cancer therapeutic.
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