A simple approach to novel 1,3-diamino-1,3-dideoxydihydrosphingosines

A short and flexible construction of novel dihydrosphingosine-type analogues has been accomplished. The pivotal step of this approach was a cascade [3,3]-sigmatropic rearrangement of a tris(imidate) substrate, which provided the core motif of our final compounds with three carbon–nitrogen bonds, including two consecutive stereocentres, starting from an l-erythrofuranose chiron. The subsequent cross-metathesis scenario allowed for the instalment of an alkyl side chain unit. Antiproliferative/cytotoxic screening of the target derivative revealed its capacity to alter the viability of both leukaemia and solid tumour cell lines.