Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hy...

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Detalles Bibliográficos
Autores principales: Huang, Guozheng, Schramm, Simon, Heilmann, Jörg, Biedermann, David, Křen, Vladimír, Decker, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901995/
https://www.ncbi.nlm.nih.gov/pubmed/27340458
http://dx.doi.org/10.3762/bjoc.12.66
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author Huang, Guozheng
Schramm, Simon
Heilmann, Jörg
Biedermann, David
Křen, Vladimír
Decker, Michael
author_facet Huang, Guozheng
Schramm, Simon
Heilmann, Jörg
Biedermann, David
Křen, Vladimír
Decker, Michael
author_sort Huang, Guozheng
collection PubMed
description Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields.
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spelling pubmed-49019952016-06-23 Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins Huang, Guozheng Schramm, Simon Heilmann, Jörg Biedermann, David Křen, Vladimír Decker, Michael Beilstein J Org Chem Full Research Paper Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields. Beilstein-Institut 2016-04-08 /pmc/articles/PMC4901995/ /pubmed/27340458 http://dx.doi.org/10.3762/bjoc.12.66 Text en Copyright © 2016, Huang 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
Huang, Guozheng
Schramm, Simon
Heilmann, Jörg
Biedermann, David
Křen, Vladimír
Decker, Michael
Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title_full Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title_fullStr Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title_full_unstemmed Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title_short Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
title_sort unconventional application of the mitsunobu reaction: selective flavonolignan dehydration yielding hydnocarpins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901995/
https://www.ncbi.nlm.nih.gov/pubmed/27340458
http://dx.doi.org/10.3762/bjoc.12.66
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