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

An 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.

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Bibliographic Details
Main Authors: Tejedor, David, Delgado-Hernández, Samuel, Peyrac, Jesús, González-Platas, Javier, García-Tellado, Fernando
Other Authors: Ministerio de Economía y Competitividad (España)
Format: artículo biblioteca
Language:English
Published: John Wiley & Sons 2017-07-26
Online Access:http://hdl.handle.net/10261/164683
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100003329
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