Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Opt...

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Autores principales: Zaragozá, Ramón J., González-Cardenete, Miguel A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9052302/
https://www.ncbi.nlm.nih.gov/pubmed/35497114
http://dx.doi.org/10.1039/d0ra02711a
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author Zaragozá, Ramón J.
González-Cardenete, Miguel A.
author_facet Zaragozá, Ramón J.
González-Cardenete, Miguel A.
author_sort Zaragozá, Ramón J.
collection PubMed
description The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
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spelling pubmed-90523022022-04-29 Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction Zaragozá, Ramón J. González-Cardenete, Miguel A. RSC Adv Chemistry The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid. The Royal Society of Chemistry 2020-04-16 /pmc/articles/PMC9052302/ /pubmed/35497114 http://dx.doi.org/10.1039/d0ra02711a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zaragozá, Ramón J.
González-Cardenete, Miguel A.
Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title_full Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title_fullStr Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title_full_unstemmed Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title_short Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
title_sort synthesis of bodinieric acids a and b, both c-18 and c-19-functionalized abietane diterpenoids: dft study of the key aldol reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9052302/
https://www.ncbi.nlm.nih.gov/pubmed/35497114
http://dx.doi.org/10.1039/d0ra02711a
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AT gonzalezcardenetemiguela synthesisofbodiniericacidsaandbbothc18andc19functionalizedabietanediterpenoidsdftstudyofthekeyaldolreaction

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