Synthesis and in vitro cytotoxic evaluation of spiro-β-lactone-γ-lactam scaffolds

Abstract A successful approach to the construction of spiro-β-lactone-γ-lactam synthons 5 and ent-5 as a similar structural motif present in natural products such as oxazolomycins was developed. Two chirons, the protected 3-isothiocyanato-3-C-vinyl-α- d -xylofuranose and its antipode, were employed as the starting material. In order to obtain a lactone-pyrrolidine cyclic framework, a ring-closing metathesis, a highly diastereoselective reduction of a double bond and the formation of a β-lactone skeleton were involved as the key transformations. The final enantiomeric pharmacophores were screened for their capacity to alter the viability of cancer cells.