A simple approach to orthogonally protected 2,3-diaminopropanols: intermediates for l- and d-Dap-containing
Kvetoslava Stanková1, Gabriela Ondrejkovičová1, Miroslava Martinková1
1Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic.
Abstract:
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.
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