Synthesis of (+/-) mappicine and mappicine ketone

✍ Scribed by Kevin E. Henegar; Ted A. Baughman

• Book ID: 102340948
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 46 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400407

✦ Synopsis

Abstract

Mappicine and mappicine ketone are camptothecin analogs of interest as antiviral agents. A novel synthesis of these compounds is described using a Friedlander condensation. The requisite ketone is prepared via a regioselective ortho‐directed metallation/alkylation of a trisubstituted pyridine. This is condensed with N‐t‐butyloxycarbonyl‐o‐aminobenzaldehyde as a convenient, stable o‐aminobenzaldehyde equivalent in the Friedlander condensation.