The first total synthesis of 15-epi-annonin I

Article abstract of DOI:10.1016/0040-4039(96)01589-4

The first total synthesis of the 15-epimer 1b of the naturally occurring acetogenin annonin I 1a is described. All stereogenic centres in the bis-THF subunit are controlled via successive Sharpless asymmetric epoxidations (AE). Alkyl side chains were attached directly to the core using alkyne-epoxide couplings.