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从柚皮苷合成黄腐酚和黄腐酚 -d。

Synthesis of xanthohumol and xanthohumol-d from naringenin.

作者信息

Andrusiak Joanna, Mylkie Kinga, Wysocka Małgorzata, Ścianowski Jacek, Wolan Andrzej, Budny Marcin

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University Gagarina 7 87-100 Toruń Poland.

Synthex Technologies Sp. z o.o. Gagarina 7/134B 87-100 Toruń Poland

出版信息

RSC Adv. 2021 Aug 31;11(46):28934-28939. doi: 10.1039/d1ra05443k. eCollection 2021 Aug 23.

DOI:10.1039/d1ra05443k
PMID:35478583
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9038150/
Abstract

A six-step synthesis of xanthohumol (1a) and its d-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.

摘要

报道了一种从易于获得的柚皮素出发合成黄腐酚（1a）及其 d-衍生物（1b）的六步合成方法。通过 Mitsunobu 反应引入异戊烯基侧链，随后进行铕催化的克莱森重排，再经碱介导的色满酮开环反应得到α,β-共轭酮体系。化合物 1b 在两种波兰啤酒中用作 1a 的稳定同位素稀释分析的内标。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e70f/9038150/f1dfe7cb9174/d1ra05443k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e70f/9038150/b572456d4793/d1ra05443k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e70f/9038150/f1dfe7cb9174/d1ra05443k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e70f/9038150/b572456d4793/d1ra05443k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e70f/9038150/f1dfe7cb9174/d1ra05443k-s2.jpg

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