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Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()

The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto a...

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Detalles Bibliográficos
Autores principales: Anderson, James C., Grounds, Helen, Reeves, Suzanna, Taylor, Peter W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Pergamon Press 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4006114/
https://www.ncbi.nlm.nih.gov/pubmed/24876661
http://dx.doi.org/10.1016/j.tet.2014.03.052
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author Anderson, James C.
Grounds, Helen
Reeves, Suzanna
Taylor, Peter W.
author_facet Anderson, James C.
Grounds, Helen
Reeves, Suzanna
Taylor, Peter W.
author_sort Anderson, James C.
collection PubMed
description The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation.
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spelling pubmed-40061142014-05-27 Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance() Anderson, James C. Grounds, Helen Reeves, Suzanna Taylor, Peter W. Tetrahedron Article The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation. Pergamon Press 2014-05-27 /pmc/articles/PMC4006114/ /pubmed/24876661 http://dx.doi.org/10.1016/j.tet.2014.03.052 Text en © 2014 The Authors http://creativecommons.org/licenses/by/3.0/ This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Anderson, James C.
Grounds, Helen
Reeves, Suzanna
Taylor, Peter W.
Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title_full Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title_fullStr Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title_full_unstemmed Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title_short Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
title_sort improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance()
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4006114/
https://www.ncbi.nlm.nih.gov/pubmed/24876661
http://dx.doi.org/10.1016/j.tet.2014.03.052
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