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syntheses of sulfur flavan-3-ol analogues 1-8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2010-08, Vol.15 (8), p.5595-5619
Main Authors: Sharma, Pradeep K, He, Min, Jurayj, Jurjus, Gou, Da-Ming, Lombardy, Richard, Romanczyk, Jr, Leo J, Schroeter, Hagen
Format: Article
Language:English
Subjects:
5,7-dideoxythiocatechin
5,7-dideoxythioepicatechin
Apoptosis
asymmetric dihydroxylation
Cell cycle
Cocoa
Cyclization
flavan-3-ols
Flavonoids
Flavonoids - chemical synthesis
Flavonoids - chemistry
Metabolism
Metabolites
Oxidation
Rotation
Stereoisomerism
Sulfur
Sulfur Compounds - chemical synthesis
Sulfur Compounds - chemistry
thiocatechin
thioepicatechin
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Summary: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syntheses of sulfur flavan-3-ol analogues 1-8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules15085595