Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide‐Based Drug Development Candidate1. (26th February 2015)

• Record Type: Journal Article
• Authors: Ding, Hui; DeRoy, Patrick L.; Perreault, Christian; Larivée, Alexandre; Siddiqui, Arshad; Caldwell, Charles G.; Harran, Susan; Harran, Patrick G.
• Is Part Of: Angewandte Chemie. Volume 127:Number 16(2015)
• Page Start: 4900
• Page End: 4904
• Publication Date: 2015-02-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201411663
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>