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Tejedor D, Delgado-Hernández S, Peyrac J, et al. Integrative Pericyclic Cascade: An Atom Economic, Multi C-C Bond-Forming Strategy for the Construction of Molecular Complexity. Chemistry. 2017;23(42):10048-10052doi: 10.1002/chem.201702667.
Tejedor, D., Delgado-Hernández, S., Peyrac, J., González-Platas, J., & García-Tellado, F. (2017). Integrative Pericyclic Cascade: An Atom Economic, Multi C-C Bond-Forming Strategy for the Construction of Molecular Complexity. Chemistry (Weinheim an der Bergstrasse, Germany), 23(42), 10048-10052. https://doi.org/10.1002/chem.201702667
Tejedor, David, et al. "Integrative Pericyclic Cascade: An Atom Economic, Multi C-C Bond-Forming Strategy for the Construction of Molecular Complexity." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,42 (2017): 10048-10052. doi: https://doi.org/10.1002/chem.201702667
Tejedor D, Delgado-Hernández S, Peyrac J, González-Platas J, García-Tellado F. Integrative Pericyclic Cascade: An Atom Economic, Multi C-C Bond-Forming Strategy for the Construction of Molecular Complexity. Chemistry. 2017 Jul 26;23(42):10048-10052. doi: 10.1002/chem.201702667. Epub 2017 Jul 11. PMID: 28621466.
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Chemistry. 2017 Jul 26;23(42):10048-10052. doi: 10.1002/chem.201702667. Epub 2017 Jul 11.

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

Chemistry (Weinheim an der Bergstrasse, Germany)

David Tejedor, Samuel Delgado-Hernández, Jesús Peyrac, Javier González-Platas, Fernando García-Tellado

Affiliations

  1. Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Astrofísico Francisco Sánchez 3, 38206, La Laguna, Tenerife, Spain.
  2. Servicio de Difracción de Rayos X, Departamento de Física, Universidad de La Laguna, Astrofísico Francisco Sánchez 2, 38204, La Laguna, Tenerife, Spain.

PMID: 28621466 DOI: 10.1002/chem.201702667

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.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: domino; molecular complexity; pericyclic reactions; polycycles; propargyl vinyl ethers.

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