Synthesis and in vitro anticancer activity of penaresidin-related stereoisomeric analogues

Abstract

A straightforward route to penaresidin-based derivatives with an unsubstituted alkyl side chain was developed. To construct these stereoisomeric azetidene-derived alkaloids, [3,3]-sigmatropic rearrangements followed by late stage olefin cross metathesis and an intramolecular nucleophilic type substitution were involved as the key transformations. The protected d-ribofuranose was chosen as the sole chiral source. The ability of target molecules to inhibit cancer cells proliferation was evaluated on a panel of five malignant cell lines.

Keywords: Azetidine skeleton; Cytotoxic activity; Olefin cross metathesis; Penaresidins; [3,3]-sigmatropic rearrangement.