The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF(3)·OEt(2) or PIFA in BF(3)·OEt(2) in 7–8%...

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Autores principales: Daley, Sharna-kay, Downer-Riley, Nadale
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7445397/
https://www.ncbi.nlm.nih.gov/pubmed/32874349
http://dx.doi.org/10.3762/bjoc.16.169
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author Daley, Sharna-kay
Downer-Riley, Nadale
author_facet Daley, Sharna-kay
Downer-Riley, Nadale
author_sort Daley, Sharna-kay
collection PubMed
description The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF(3)·OEt(2) or PIFA in BF(3)·OEt(2) in 7–8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps.
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spelling pubmed-74453972020-08-31 The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization Daley, Sharna-kay Downer-Riley, Nadale Beilstein J Org Chem Full Research Paper The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF(3)·OEt(2) or PIFA in BF(3)·OEt(2) in 7–8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps. Beilstein-Institut 2020-08-18 /pmc/articles/PMC7445397/ /pubmed/32874349 http://dx.doi.org/10.3762/bjoc.16.169 Text en Copyright © 2020, Daley and Downer-Riley https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Daley, Sharna-kay
Downer-Riley, Nadale
The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title_full The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title_fullStr The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title_full_unstemmed The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title_short The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
title_sort biomimetic synthesis of balsaminone a and ellagic acid via oxidative dimerization
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7445397/
https://www.ncbi.nlm.nih.gov/pubmed/32874349
http://dx.doi.org/10.3762/bjoc.16.169
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