Total Synthesis of Melonine

Total synthesis of melonine was accomplished. A cycloheptene unit and a quinoline unit were connected via Stille coupling. The quinoline core was cleaved with thiophosgene to liberate the arylamine moiety. Oxidative intramolecular aziridination, followed by intramolecular nucleophilic attack of the arylamine moiety to the aziridine ring, constructed the characteristic cyclic system with the <i>trans</i>-1,2-diamine structure. Stereoselective hydrogenation and the formation of a piperidine ring led to the synthesis of melonine.