A straightforward approach toward cytotoxic pyrrolidine alkaloids: Novel analogues of natural broussonetines

Straightforward access to a series of the cytotoxic sphingolipid-derived alkaloids possessing a pyrrolidine unit and a long hydrophobic side chain was accomplished. Two simple carbohydrate chirons, protected d- and l-erythrofuranose, were chosen as the starting material, and [3,3]-sigmatropic rearrangements, a late stage cross metathesis and an intramolecular nucleophilic substitution were involved as the key transformations. The final analogues of natural broussonetines were evaluated for their capacity to alter the proliferation of cancer cells. [Display omitted] •Synthesis of novel straight side chain broussonetine analogues was accomplished.•The used strategy relied on [3,3]-sigmatropic rearrangements, the OCM reaction and SN2 cyclization.•The stereochemistry of a key substructure was determined via crystallographic analysis.•The target pyrrolidine-based alkaloids exhibit an ability to inhibit cancer cell proliferation.