Piperidones: from alkaloids to pseudopeptides

Abstract

Our early work on the synthesis of alkaloids that contain a piperidine ring led us to prepare diversely functionalised piperidines as scaffolds for building more complex structures. Since then we have prepared a number of piperidone synthons, and we have applied these to the preparation of biologically interesting compounds which range from alkaloids to conformationally constrained pseudopeptides. We provide here a brief historical introduction, followed by eight sections, dedicated to our most relevant piperidine synthons: i) 2-aryl-4-piperidones, ii) ∆3-piperidein-2-ones and 2-cyanopiperideines, iii) 3-amino-2-arylpiperidin-4-ones, iv) 3-aminopiperidin-2-ones, v) glutarimides, vi) 3-amino-∆5- piperidein-2-ones, vii) oxazolopiperidones, and viii) hydroxylactams.