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Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling

A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reactio...

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Detalles Bibliográficos
Autores principales: Aimon, Anthony, Farrugia, Louis J., Clark, J. Stephen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680490/
https://www.ncbi.nlm.nih.gov/pubmed/31336669
http://dx.doi.org/10.3390/molecules24142654
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author Aimon, Anthony
Farrugia, Louis J.
Clark, J. Stephen
author_facet Aimon, Anthony
Farrugia, Louis J.
Clark, J. Stephen
author_sort Aimon, Anthony
collection PubMed
description A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor.
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spelling pubmed-66804902019-08-09 Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling Aimon, Anthony Farrugia, Louis J. Clark, J. Stephen Molecules Article A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor. MDPI 2019-07-22 /pmc/articles/PMC6680490/ /pubmed/31336669 http://dx.doi.org/10.3390/molecules24142654 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Aimon, Anthony
Farrugia, Louis J.
Clark, J. Stephen
Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title_full Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title_fullStr Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title_full_unstemmed Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title_short Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
title_sort synthesis of the core framework of the cornexistins by intramolecular nozaki-hiyama-kishi coupling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680490/
https://www.ncbi.nlm.nih.gov/pubmed/31336669
http://dx.doi.org/10.3390/molecules24142654
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