Irreversible endo ‐Selective Diels–Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo ‐Cantharimides - Normandie Université Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2015

Irreversible endo ‐Selective Diels–Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo ‐Cantharimides

Résumé

Abstract The [4+2] cycloaddition of 3‐alkoxyfurans with N‐substituted maleimides provides the first general route for preparing endo ‐cantharimides. Unlike the corresponding reaction with 3 H furans, the reaction can tolerate a broad range of 2‐substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead‐like properties for medicinal chemistry programs. Furthermore, the electron‐rich furans are shown to react with a variety of alternative dienophiles to generate 7‐oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3‐alkoxy group on a furan Diels–Alder reaction.

Domaines

Chimie

Dates et versions

hal-04344195 , version 1 (14-12-2023)

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Paternité

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Citer

Robert Foster, Laure Benhamou, Michael Porter, Dejan‐krešimir Bučar, Helen Hailes, et al.. Irreversible endo ‐Selective Diels–Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo ‐Cantharimides. Chemistry - A European Journal, 2015, 21 (16), pp.6107-6114. ⟨10.1002/chem.201406286⟩. ⟨hal-04344195⟩

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