Pyranone natural products as inspirations for catalytic reaction discovery and development

Accounts of Chemical Research
Benjamin R McDonald, Karl A Scheidt

Abstract

Natural products continue to provide a wealth of opportunities in the areas of chemical and therapeutic development. These structures are effective measuring sticks for the current state of chemical synthesis as a field and constantly inspire new approaches and strategies. Tetrahydropryans and tetrahydropyran-4-ones are found in numerous bioactive marine natural products and medicinal compounds. Our interest in exploring the therapeutic potential of natural products containing these motifs provided the impetus to explore new methods to access highly functionalized, chiral pyran molecules in the most direct and rapid fashion possible. This goal led to exploration and development of a Lewis acid-mediated Prins reaction between a chiral β-hydroxy-dioxinone and aldehyde to produce a pyran-dioxinone fused product that can be processed in a single pot operation to the desired tetrahydropyran-4-ones in excellent yield and stereoselectivity. Although the Prins reaction is a commonly employed approach toward pyrans, this method uniquely provides a 3-carboxy-trisubstituted pyran and utilizes dioxinones in a manner that was underexplored at the time. The 3-carboxy substituent served as a key synthetic handhold when this method was applied...Continue Reading

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Citations

Feb 18, 2016·Chemical Communications : Chem Comm·Sergio J Álvarez-MéndezVíctor S Martín
Jul 18, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jan BojanowskiAnna Albrecht
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jan Bojanowski, Anna Albrecht
Jul 24, 2018·The Journal of Organic Chemistry·Sergio J Álvarez-MéndezVíctor S Martín

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