Synthesis of dizocilpine

A simple five-step synthetic route toward dizocilpine (1) starting with dibenzosuberenone (2) in 28% of total yield is described. The facile route was carried from by aziridination of dibenzosuberenone (2) with NBS and chloramines-T in MeCN at reflux, hydrogenolysis of azridinyl ketone, Grignard methylation of amino ketone, BF3·OEt2-promoted cyclization of amino alcohol, and desulfonylation with Mg and Et3N in MeOH. Anthracene skeleton 9 is also synthesized via an intramolecular rearrangement of pinacol to pinacolone.

Figure optionsDownload as PowerPoint slide