Total Synthesis of the Bacterial ortho -Quinol (+)-Strepantibin A through Iodyl-Type λ 5 -Iodane-Promoted Asymmetric Hydroxylative Phenol Dearomatization.

An enantioselective synthesis of the bacterial metabolite (+)-strepantibin A, a novel inhibitor of the hexokinase II (HK2) in cancer cells, is described. Its monomethylated resorcinolic para -terphenyl core was conveniently prepared through a Danheiser benzannulation. The elaboration of its ortho -quinolic chiral center was accomplished by relying on an iodyl-promoted regio- and enantioselective hydroxylative dearomatization. The olefinic side-chain of the resulting ortho -quinol was finally oxygenated under Wacker-type conditions to generate the propanone appendage of (+)-strepantibin A.