Stereoselective synthesis of (+)-IKD-8344

Total synthesis of IKD-8344 was accomplished via stepwise cyclodimerization of the monomeric seco acid under Yamaguchi conditions. In the synthesis of the monomeric seco acid, Wittig olefination reaction was employed for an efficient bond formation at C7–C8. The threo-trans oxolane unit for the rings a and c was prepared via intramolecular Williamson ether synthesis of the hydroxyl mesylate prepared via asymmetric aldol reaction. Radical cyclization of a β-alkoxymethacrylate intermediate furnished the threo-cis oxolane unit for the b ring fragment.