Vicinal ketoesters – key intermediates in the total synthesis of natural products

This review summarizes examples for the application of vicinal ketoesters such as α-ketoesters, mesoxalic esters, and α,β-diketoesters as key intermediates in the total synthesis of natural products utilizing their electrophilic keto group as reactive site. Suitable key reactions are, e.g., aldol ad...

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Detalles Bibliográficos
Autores principales: Beller, Marc Paul, Koert, Ulrich
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Review
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490073/
https://www.ncbi.nlm.nih.gov/pubmed/36158171
http://dx.doi.org/10.3762/bjoc.18.129
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author Beller, Marc Paul
Koert, Ulrich
author_facet Beller, Marc Paul
Koert, Ulrich
author_sort Beller, Marc Paul
collection PubMed
description This review summarizes examples for the application of vicinal ketoesters such as α-ketoesters, mesoxalic esters, and α,β-diketoesters as key intermediates in the total synthesis of natural products utilizing their electrophilic keto group as reactive site. Suitable key reactions are, e.g., aldol additions, carbonyl ene reactions, Mannich reactions, and additions of organometallic reagents. The vicinal arrangement of carbonyl groups allows the stabilization of reactive conformations by chelation or dipole control.
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spelling pubmed-94900732022-09-23 Vicinal ketoesters – key intermediates in the total synthesis of natural products Beller, Marc Paul Koert, Ulrich Beilstein J Org Chem Review This review summarizes examples for the application of vicinal ketoesters such as α-ketoesters, mesoxalic esters, and α,β-diketoesters as key intermediates in the total synthesis of natural products utilizing their electrophilic keto group as reactive site. Suitable key reactions are, e.g., aldol additions, carbonyl ene reactions, Mannich reactions, and additions of organometallic reagents. The vicinal arrangement of carbonyl groups allows the stabilization of reactive conformations by chelation or dipole control. Beilstein-Institut 2022-09-15 /pmc/articles/PMC9490073/ /pubmed/36158171 http://dx.doi.org/10.3762/bjoc.18.129 Text en Copyright © 2022, Beller and Koert https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Review
Beller, Marc Paul
Koert, Ulrich
Vicinal ketoesters – key intermediates in the total synthesis of natural products
title Vicinal ketoesters – key intermediates in the total synthesis of natural products
title_full Vicinal ketoesters – key intermediates in the total synthesis of natural products
title_fullStr Vicinal ketoesters – key intermediates in the total synthesis of natural products
title_full_unstemmed Vicinal ketoesters – key intermediates in the total synthesis of natural products
title_short Vicinal ketoesters – key intermediates in the total synthesis of natural products
title_sort vicinal ketoesters – key intermediates in the total synthesis of natural products
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490073/
https://www.ncbi.nlm.nih.gov/pubmed/36158171
http://dx.doi.org/10.3762/bjoc.18.129
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