Polyhydroxylated piperidines, or aminoglycoside mimics, have recently attracted the attention of the synthetic community due to their glycosidase inhibitory properties. These properties make them powerful candidates in the treatment of various diseases including cancer and HIV. These nitrogen containing heterocycles that behave much like sugars can be grouped into five structural classes: polyhydroxylated piperidines, pyrrolidines, indolizidines, pyrrolizidines, and nortropanes. We have recently reported the generation of seven membered nitrogen heterocycles via a 4+3 cycloadditon that proceeds through an aza-oxyallycation intermediate. It was demonstrated that the heterocycle could be functionalized with a chlorine atom providing entry into the polyhdroxylated piperidine class of alkaloids. Recent progress towards the synthesis of these molecules as well as method development will be presented.

Development of a short and concise synthesis of aminoglycoside mimics

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.