Total synthesis of (-)-aplaminal by Buchwald-Hartwig cross-coupling of an aminal

The concise total synthesis of an unusual alkaloid, aplaminal, has been accomplished. The synthetic feature is the Buchwald-Hartwig cross-coupling between a novel triazabicyclo[3.2.1]octane core and an aromatic bromide. The practicality of our approach provides aplaminal analogs and preliminary structure-cytotoxicity relationships of an aromatic moiety were achieved.