Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4′-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4′-O-methyl-5-O-prenyl-7-O-benzylkaempferol (8) via para-Cla...

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Detalles Bibliográficos
Autores principales: Mei, Qinggang, Wang, Chun, Zhao, Zhigang, Yuan, Weicheng, Zhang, Guolin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578360/
https://www.ncbi.nlm.nih.gov/pubmed/26425179
http://dx.doi.org/10.3762/bjoc.11.135
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author Mei, Qinggang
Wang, Chun
Zhao, Zhigang
Yuan, Weicheng
Zhang, Guolin
author_facet Mei, Qinggang
Wang, Chun
Zhao, Zhigang
Yuan, Weicheng
Zhang, Guolin
author_sort Mei, Qinggang
collection PubMed
description The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4′-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4′-O-methyl-5-O-prenyl-7-O-benzylkaempferol (8) via para-Claisen–Cope rearrangement catalyzed by Eu(fod)(3) in the presence of NaHCO(3), and the glycosylation of icaritin (3) are the key steps.
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spelling pubmed-45783602015-09-30 Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement Mei, Qinggang Wang, Chun Zhao, Zhigang Yuan, Weicheng Zhang, Guolin Beilstein J Org Chem Full Research Paper The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4′-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4′-O-methyl-5-O-prenyl-7-O-benzylkaempferol (8) via para-Claisen–Cope rearrangement catalyzed by Eu(fod)(3) in the presence of NaHCO(3), and the glycosylation of icaritin (3) are the key steps. Beilstein-Institut 2015-07-20 /pmc/articles/PMC4578360/ /pubmed/26425179 http://dx.doi.org/10.3762/bjoc.11.135 Text en Copyright © 2015, Mei et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Mei, Qinggang
Wang, Chun
Zhao, Zhigang
Yuan, Weicheng
Zhang, Guolin
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title_full Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title_fullStr Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title_full_unstemmed Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title_short Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
title_sort synthesis of icariin from kaempferol through regioselective methylation and para-claisen–cope rearrangement
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578360/
https://www.ncbi.nlm.nih.gov/pubmed/26425179
http://dx.doi.org/10.3762/bjoc.11.135
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