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Integrative Pericyclic Cascade: An Atom Economic, Multi C−C Bond‐Forming Strategy for the Construction of Molecular Complexity

AuthorsTejedor, David ; Delgado-Hernández, Samuel; Peyrac, Jesús; González-Platas, Javier; García-Tellado, Fernando
Issue Date26-Jul-2017
PublisherJohn Wiley & Sons
CitationChemistry - a European Journal 23(42): 10048-10052 (2017)
AbstractAn all‐pericyclic manifold is developed for the construction of topologically diverse, structurally complex and natural product‐like polycyclic chemotypes. The manifold uses readily accessible tertiary propargyl vinyl ethers as substrates and imidazole as a catalyst to form up to two new rings, three new C−C bonds, six stereogenic centers and one transannular oxo‐bridge. The manifold is efficient, scalable and instrumentally simple to perform and entails a propargyl Claisen rearrangement–[1,3]H shift, an oxa‐6π‐electrocyclization, and an intramolecular Diels–Alder reaction.
Publisher version (URL)https://doi.org/10.1002/chem.201702667
Appears in Collections:(IPNA) Artículos
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