Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring

摘要

This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-beta-D-ribofuranosyl)thiazole-4-carboxamide (2',3'-anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides. The synthetic approach was based on a multistep transformation of D-glucose into suitably protected aldonthioamides followed by their subsequent cyclocondensation with ethyl bromopyruvate to form the thiazole ring. Antiproliferative activity of the target molecules is reported against several human tumour cell lines.