Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

The first enantioselective syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom. The key steps were: (a) Pd(0) catalyzed introduction of –S t-butyl group, (b) Sharpless enantioselective dihydroxylation of t...

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Autores principales: Sharma, Pradeep K., He, Min, Jurayj, Jurjus, Gou, Da-Ming, Lombardy, Richard, Jr., Leo J. Romanczyk, Schroeter, Hagen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257781/
https://www.ncbi.nlm.nih.gov/pubmed/20714315
http://dx.doi.org/10.3390/molecules15085595
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author Sharma, Pradeep K.
He, Min
Jurayj, Jurjus
Gou, Da-Ming
Lombardy, Richard
Jr., Leo J. Romanczyk
Schroeter, Hagen
author_facet Sharma, Pradeep K.
He, Min
Jurayj, Jurjus
Gou, Da-Ming
Lombardy, Richard
Jr., Leo J. Romanczyk
Schroeter, Hagen
author_sort Sharma, Pradeep K.
collection PubMed
description The first enantioselective syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom. The key steps were: (a) Pd(0) catalyzed introduction of –S t-butyl group, (b) Sharpless enantioselective dihydroxylation of the alkene, (c) acid catalyzed ring closure to produce the thiopyran ring, and (d) removal of benzyl groups using N,N-dimethylaniline and AlCl(3). The compounds were isolated in high chemical and optical purity.
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spelling pubmed-62577812018-12-06 Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols Sharma, Pradeep K. He, Min Jurayj, Jurjus Gou, Da-Ming Lombardy, Richard Jr., Leo J. Romanczyk Schroeter, Hagen Molecules Article The first enantioselective syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom. The key steps were: (a) Pd(0) catalyzed introduction of –S t-butyl group, (b) Sharpless enantioselective dihydroxylation of the alkene, (c) acid catalyzed ring closure to produce the thiopyran ring, and (d) removal of benzyl groups using N,N-dimethylaniline and AlCl(3). The compounds were isolated in high chemical and optical purity. MDPI 2010-08-13 /pmc/articles/PMC6257781/ /pubmed/20714315 http://dx.doi.org/10.3390/molecules15085595 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an Open Access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Sharma, Pradeep K.
He, Min
Jurayj, Jurjus
Gou, Da-Ming
Lombardy, Richard
Jr., Leo J. Romanczyk
Schroeter, Hagen
Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title_full Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title_fullStr Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title_full_unstemmed Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title_short Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
title_sort enantioselctive syntheses of sulfur analogues of flavan-3-ols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257781/
https://www.ncbi.nlm.nih.gov/pubmed/20714315
http://dx.doi.org/10.3390/molecules15085595
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