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

Abstract

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.