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Integrative Pericyclic Cascade: An Atom Economic, Multi C−C Bond‐Forming Strategy for the Construction of Molecular Complexity
Author(s) -
Tejedor David,
DelgadoHernández Samuel,
Peyrac Jesús,
GonzálezPlatas Javier,
GarcíaTellado Fernando
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702667
Subject(s) - pericyclic reaction , cascade , atom (system on chip) , bond , atom economy , chemistry , computer science , nanotechnology , computational chemistry , business , materials science , catalysis , organic chemistry , parallel computing , finance , chromatography
Abstract 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.