Total synthesis of the potent antitumor, bis-tetrahydrofuranyl annonaceous acetogenins (+)-asimicin and (+)-bullatacin

Article abstract of DOI:10.1016/0040-4039(95)00207-S

Convergent syntheses of the title compounds involve: a bis-THF-subunit preparation via Sharpless' double asymmetric dihydroxylation and subsequent asymmetric epoxidation; preparation of the C(4)-hydroxybutenolide-containing subunit using a Stille butenolide synthesis: Pd°-mediated coupling of these vinyl iodide and alkyne subunits; and selective Wilkinson reduction of the resulting enyne.