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Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid

Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subs...

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Autores principales: Kuntiyong, Punlop, Namborisut, Duangkamon, Phakdeeyothin, Kunita, Chatpreecha, Rungrawin, Thammapichai, Kittisak
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512815/
https://www.ncbi.nlm.nih.gov/pubmed/34641410
http://dx.doi.org/10.3390/molecules26195866
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author Kuntiyong, Punlop
Namborisut, Duangkamon
Phakdeeyothin, Kunita
Chatpreecha, Rungrawin
Thammapichai, Kittisak
author_facet Kuntiyong, Punlop
Namborisut, Duangkamon
Phakdeeyothin, Kunita
Chatpreecha, Rungrawin
Thammapichai, Kittisak
author_sort Kuntiyong, Punlop
collection PubMed
description Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subsequent regioselective hydride reduction of the glutarimide carbonyl followed by N-acyliminium ion cyclization afforded a product with opposite absolute configurations at C3 and C11b. Cope elimination of the dibenzylamino group then converted the two diastereomers into enantiomers.
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spelling pubmed-85128152021-10-14 Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid Kuntiyong, Punlop Namborisut, Duangkamon Phakdeeyothin, Kunita Chatpreecha, Rungrawin Thammapichai, Kittisak Molecules Article Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subsequent regioselective hydride reduction of the glutarimide carbonyl followed by N-acyliminium ion cyclization afforded a product with opposite absolute configurations at C3 and C11b. Cope elimination of the dibenzylamino group then converted the two diastereomers into enantiomers. MDPI 2021-09-28 /pmc/articles/PMC8512815/ /pubmed/34641410 http://dx.doi.org/10.3390/molecules26195866 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
Kuntiyong, Punlop
Namborisut, Duangkamon
Phakdeeyothin, Kunita
Chatpreecha, Rungrawin
Thammapichai, Kittisak
Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title_full Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title_fullStr Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title_full_unstemmed Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title_short Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid
title_sort enantiodivergent synthesis of benzoquinolizidinones from l-glutamic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512815/
https://www.ncbi.nlm.nih.gov/pubmed/34641410
http://dx.doi.org/10.3390/molecules26195866
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