Stereoselective synthesis of Sch 642305, an inhibitor of bacterial DNA primase

Sch 642305 is a fungal nonanolide, which inhibits bacterial DNA primase and HIV-1 Tat transactivation. The enantioselective synthesis of Sch 642305 was succeeded starting from useful chiral building block via stereoselective dianion alkylation of β-ketosulfoxide and lactonization.

Graphical Abstract