A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A

[Image: see text] We report the first asymmetric, total synthesis of (−)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the...

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Autores principales: McDonald, Benjamin R., Nibbs, Antoinette E., Scheidt, Karl A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284651/
https://www.ncbi.nlm.nih.gov/pubmed/25517432
http://dx.doi.org/10.1021/ol503303w
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author McDonald, Benjamin R.
Nibbs, Antoinette E.
Scheidt, Karl A.
author_facet McDonald, Benjamin R.
Nibbs, Antoinette E.
Scheidt, Karl A.
author_sort McDonald, Benjamin R.
collection PubMed
description [Image: see text] We report the first asymmetric, total synthesis of (−)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.
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spelling pubmed-42846512015-01-07 A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A McDonald, Benjamin R. Nibbs, Antoinette E. Scheidt, Karl A. Org Lett [Image: see text] We report the first asymmetric, total synthesis of (−)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products. American Chemical Society 2014-12-17 2015-01-02 /pmc/articles/PMC4284651/ /pubmed/25517432 http://dx.doi.org/10.1021/ol503303w Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle McDonald, Benjamin R.
Nibbs, Antoinette E.
Scheidt, Karl A.
A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title_full A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title_fullStr A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title_full_unstemmed A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title_short A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A
title_sort biomimetic strategy to access the silybins: total synthesis of (−)-isosilybin a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284651/
https://www.ncbi.nlm.nih.gov/pubmed/25517432
http://dx.doi.org/10.1021/ol503303w
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