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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Integrative Pericyclic Cascade: An Atom Economic, Multi C-C Bond-Forming Strategy for the Construction of Molecular
David Tejedor1, Samuel Delgado-Hernández1, Jesús Peyrac1
1Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Astrofísico Francisco Sánchez 3, 38206, La Laguna, Tenerife, Spain.
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.
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