Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent

2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-d-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species. The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure–activity relationship.