Total Synthesis of (+)‐Cornexistin

Herein, we describe the first total synthesis of (+)‐cornexistin as well as its 8‐epi‐isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary‐controlled syn‐Evans‐aldol reaction, and a highly efficient intramolecular alkylation to form the...

Descripción completa

Detalles Bibliográficos
Autores principales: Steinborn, Christian, Wildermuth, Raphael E., Barber, David M., Magauer, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540023/
https://www.ncbi.nlm.nih.gov/pubmed/32558114
http://dx.doi.org/10.1002/anie.202008158
_version_ 1783591136961495040
author Steinborn, Christian
Wildermuth, Raphael E.
Barber, David M.
Magauer, Thomas
author_facet Steinborn, Christian
Wildermuth, Raphael E.
Barber, David M.
Magauer, Thomas
author_sort Steinborn, Christian
collection PubMed
description Herein, we describe the first total synthesis of (+)‐cornexistin as well as its 8‐epi‐isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary‐controlled syn‐Evans‐aldol reaction, and a highly efficient intramolecular alkylation to form the nine‐membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β‐keto nitrile. The developed route enabled the synthesis of 165 mg (+)‐cornexistin.
format Online
Article
Text
id pubmed-7540023
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-75400232020-10-09 Total Synthesis of (+)‐Cornexistin Steinborn, Christian Wildermuth, Raphael E. Barber, David M. Magauer, Thomas Angew Chem Int Ed Engl Communications Herein, we describe the first total synthesis of (+)‐cornexistin as well as its 8‐epi‐isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary‐controlled syn‐Evans‐aldol reaction, and a highly efficient intramolecular alkylation to form the nine‐membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β‐keto nitrile. The developed route enabled the synthesis of 165 mg (+)‐cornexistin. John Wiley and Sons Inc. 2020-08-18 2020-09-21 /pmc/articles/PMC7540023/ /pubmed/32558114 http://dx.doi.org/10.1002/anie.202008158 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Steinborn, Christian
Wildermuth, Raphael E.
Barber, David M.
Magauer, Thomas
Total Synthesis of (+)‐Cornexistin
title Total Synthesis of (+)‐Cornexistin
title_full Total Synthesis of (+)‐Cornexistin
title_fullStr Total Synthesis of (+)‐Cornexistin
title_full_unstemmed Total Synthesis of (+)‐Cornexistin
title_short Total Synthesis of (+)‐Cornexistin
title_sort total synthesis of (+)‐cornexistin
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540023/
https://www.ncbi.nlm.nih.gov/pubmed/32558114
http://dx.doi.org/10.1002/anie.202008158
work_keys_str_mv AT steinbornchristian totalsynthesisofcornexistin
AT wildermuthraphaele totalsynthesisofcornexistin
AT barberdavidm totalsynthesisofcornexistin
AT magauerthomas totalsynthesisofcornexistin

Ejemplares similares