Synthesis of trypanocidal tetrahydrofuran lignans

Abstract

Several tetra-substituted 2,5-dihydrofuran lignans have been prepared using a sequential Michael addition-carbocyclization with palladium as the catalyst. The synthetic compounds were evaluated against trypomastigote forms of Trypanossoma cruzi and the higher activity for diastereoisomeric compounds could be correlated to the trans configuration of the aromatic rings. The highest activity was observed for compound 14b in which IC50 was 1.5µM.