A simple approach to orthogonally protected 2,3-diaminopropanols: intermediates for l- and d-Dap-containing peptidomimetics.

A simple approach to orthogonally protected 2,3-diaminopropanols from easily available d- and l-erythrofuranose has been accomplished. The pivotal step involved a cascade Overman rearrangement to install two novel C-N bonds and create the desired diamino alcohol motif, while a one-pot ozonolysis/reductive workup accompanied by the rational execution of suitable functional group transformations allowed the carbon skeleton of the target compounds to be completed. A series of the synthesised diaminopropanols was evaluated regarding their capacity to alter proliferation of selected cancer cell lines.