A 'chiron' approach to divergent synthesis of 2-C-tridecyl 1-N-iminosugar mimetics and their anticancer profile.

Two approaches leading to 2-C-tridecyl piperidine-containing 1-N-iminosugars from the chiral pool were accomplished. The pivotal steps for completing the construction of these azasugars were aza-Claisen rearrangements as a powerful tool for the formation of carbon-nitrogen bonds, cyclisation protocols and an olefin cross-metathesis. The versatility of the developed concept permits access to other stereoisomeric partners of this class of compounds by varying the sugar unit used as the starting material. Moreover, the late-stage introduction of an alkyl branch could provide high flexibility for novel side chain analogues. Last but not least, carbohydrates are a cost-effective, environmentally biocompatible starting material for the chiral pool strategy. The preliminary cytotoxic evaluation indicates that the designed piperidines have a promising capacity to alter the viability of cancer cell lines.