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This account describes the convergent synthesis of (-)-okilactomycin. The first-generation approach focused on the assembly of two complex fragments through a Prins reaction of a dioxinone and alpha-hydroxy aldehyde. While this route was not ultimately successful, a related Maitland-Japp process employing a beta-keto ester in place of the dioxinone fragment provided the necessary union of functionalized intermediate, thereby establishing the full carbon framework of the natural product. The synthesis also employed a highly diastereoselective Lewis acid-promoted Diels-Alder reaction and an olefin ring-closing metathesis to close the strained 11-membered macrocycle of the natural product.
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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI