Total synthesis of the cytotoxic annonaceous acetogenin (30S)-bullanin

Article abstract of DOI:10.1016/S0040-4039(97)10739-0

The total synthesis of (+)-(30S)-bullanin, a highly cytotoxic Annonaceous acetogenin, was effected by a convergent approach in which the key core bis-2,2'-tetrahydrofuran stereocenters were introduced through a combination of Sharpless asymmetric dihydroxylation and S(E)2' additions of oxygenated nonracemic allylic stannane and indium reagents to γ-oxygenated aldehydes.