Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone

Total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is presented, both in racemic and enantiopure form. Our synthetic strategy involves (2S,4S)-4-hydroxyglutamic acid lactone as the key intermediate. Starting from an achiral substrate, the target stereogenic centers were introduced b...

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Autores principales: Pinčeková, Lucia, Jančiová, Eva, Berkeš, Dušan, Gyepes, Róbert, Kolarovič, Andrej, Caletková, Oľga
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10037412/
https://www.ncbi.nlm.nih.gov/pubmed/36903423
http://dx.doi.org/10.3390/molecules28052177
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author Pinčeková, Lucia
Jančiová, Eva
Berkeš, Dušan
Gyepes, Róbert
Kolarovič, Andrej
Caletková, Oľga
author_facet Pinčeková, Lucia
Jančiová, Eva
Berkeš, Dušan
Gyepes, Róbert
Kolarovič, Andrej
Caletková, Oľga
author_sort Pinčeková, Lucia
collection PubMed
description Total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is presented, both in racemic and enantiopure form. Our synthetic strategy involves (2S,4S)-4-hydroxyglutamic acid lactone as the key intermediate. Starting from an achiral substrate, the target stereogenic centers were introduced by means of crystallization-induced diastereomer transformation (CIDT) in a highly stereoselective fashion. A Maillard-type condensation was crucial to constructing the desired pyrrolic scaffold.
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spelling pubmed-100374122023-03-25 Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone Pinčeková, Lucia Jančiová, Eva Berkeš, Dušan Gyepes, Róbert Kolarovič, Andrej Caletková, Oľga Molecules Article Total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is presented, both in racemic and enantiopure form. Our synthetic strategy involves (2S,4S)-4-hydroxyglutamic acid lactone as the key intermediate. Starting from an achiral substrate, the target stereogenic centers were introduced by means of crystallization-induced diastereomer transformation (CIDT) in a highly stereoselective fashion. A Maillard-type condensation was crucial to constructing the desired pyrrolic scaffold. MDPI 2023-02-26 /pmc/articles/PMC10037412/ /pubmed/36903423 http://dx.doi.org/10.3390/molecules28052177 Text en © 2023 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
Pinčeková, Lucia
Jančiová, Eva
Berkeš, Dušan
Gyepes, Róbert
Kolarovič, Andrej
Caletková, Oľga
Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title_full Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title_fullStr Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title_full_unstemmed Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title_short Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
title_sort total synthesis of hemerocallisamine i paved by gram-scale synthesis of (2s,4s)-4-hydroxyglutamic acid lactone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10037412/
https://www.ncbi.nlm.nih.gov/pubmed/36903423
http://dx.doi.org/10.3390/molecules28052177
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