Synthesis of xanthohumol and xanthohumol-d(3) from naringenin

A six-step synthesis of xanthohumol (1a) and its d(3)-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conju...

Descripción completa

Detalles Bibliográficos
Autores principales: Andrusiak, Joanna, Mylkie, Kinga, Wysocka, Małgorzata, Ścianowski, Jacek, Wolan, Andrzej, Budny, Marcin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9038150/
https://www.ncbi.nlm.nih.gov/pubmed/35478583
http://dx.doi.org/10.1039/d1ra05443k
_version_ 1784693867411406848
author Andrusiak, Joanna
Mylkie, Kinga
Wysocka, Małgorzata
Ścianowski, Jacek
Wolan, Andrzej
Budny, Marcin
author_facet Andrusiak, Joanna
Mylkie, Kinga
Wysocka, Małgorzata
Ścianowski, Jacek
Wolan, Andrzej
Budny, Marcin
author_sort Andrusiak, Joanna
collection PubMed
description A six-step synthesis of xanthohumol (1a) and its d(3)-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers.
format Online
Article
Text
id pubmed-9038150
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90381502022-04-26 Synthesis of xanthohumol and xanthohumol-d(3) from naringenin Andrusiak, Joanna Mylkie, Kinga Wysocka, Małgorzata Ścianowski, Jacek Wolan, Andrzej Budny, Marcin RSC Adv Chemistry A six-step synthesis of xanthohumol (1a) and its d(3)-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers. The Royal Society of Chemistry 2021-08-31 /pmc/articles/PMC9038150/ /pubmed/35478583 http://dx.doi.org/10.1039/d1ra05443k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Andrusiak, Joanna
Mylkie, Kinga
Wysocka, Małgorzata
Ścianowski, Jacek
Wolan, Andrzej
Budny, Marcin
Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title_full Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title_fullStr Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title_full_unstemmed Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title_short Synthesis of xanthohumol and xanthohumol-d(3) from naringenin
title_sort synthesis of xanthohumol and xanthohumol-d(3) from naringenin
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9038150/
https://www.ncbi.nlm.nih.gov/pubmed/35478583
http://dx.doi.org/10.1039/d1ra05443k
work_keys_str_mv AT andrusiakjoanna synthesisofxanthohumolandxanthohumold3fromnaringenin
AT mylkiekinga synthesisofxanthohumolandxanthohumold3fromnaringenin
AT wysockamałgorzata synthesisofxanthohumolandxanthohumold3fromnaringenin
AT scianowskijacek synthesisofxanthohumolandxanthohumold3fromnaringenin
AT wolanandrzej synthesisofxanthohumolandxanthohumold3fromnaringenin
AT budnymarcin synthesisofxanthohumolandxanthohumold3fromnaringenin

Ejemplares similares