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Total Synthesis of the Bacterial ortho-Quinol (+)-Strepantibin A through Iodyl-Type λ5-Iodane-Promoted Asymmetric
Morgan Wloch1, Zhaozhao Sun1, Emmanuel Valzer1
1Université de Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405 Talence Cedex, France.
Abstract:
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.
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