Total Synthesis and Structural Reassignment of Laingolide A

The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type couplin...

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Autores principales: Wu, Fusong, Zhang, Tao, Yu, Jie, Guo, Yian, Ye, Tao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8145716/
https://www.ncbi.nlm.nih.gov/pubmed/33925490
http://dx.doi.org/10.3390/md19050247
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author Wu, Fusong
Zhang, Tao
Yu, Jie
Guo, Yian
Ye, Tao
author_facet Wu, Fusong
Zhang, Tao
Yu, Jie
Guo, Yian
Ye, Tao
author_sort Wu, Fusong
collection PubMed
description The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.
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spelling pubmed-81457162021-05-26 Total Synthesis and Structural Reassignment of Laingolide A Wu, Fusong Zhang, Tao Yu, Jie Guo, Yian Ye, Tao Mar Drugs Article The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide. MDPI 2021-04-27 /pmc/articles/PMC8145716/ /pubmed/33925490 http://dx.doi.org/10.3390/md19050247 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wu, Fusong
Zhang, Tao
Yu, Jie
Guo, Yian
Ye, Tao
Total Synthesis and Structural Reassignment of Laingolide A
title Total Synthesis and Structural Reassignment of Laingolide A
title_full Total Synthesis and Structural Reassignment of Laingolide A
title_fullStr Total Synthesis and Structural Reassignment of Laingolide A
title_full_unstemmed Total Synthesis and Structural Reassignment of Laingolide A
title_short Total Synthesis and Structural Reassignment of Laingolide A
title_sort total synthesis and structural reassignment of laingolide a
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8145716/
https://www.ncbi.nlm.nih.gov/pubmed/33925490
http://dx.doi.org/10.3390/md19050247
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