Cargando…
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...
Autores principales: | , , |
---|---|
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 |
_version_ | 1783441511734575104 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6680490 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT aimonanthony synthesisofthecoreframeworkofthecornexistinsbyintramolecularnozakihiyamakishicoupling AT farrugialouisj synthesisofthecoreframeworkofthecornexistinsbyintramolecularnozakihiyamakishicoupling AT clarkjstephen synthesisofthecoreframeworkofthecornexistinsbyintramolecularnozakihiyamakishicoupling |