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Molecules 2010, 15(8), 5595-5619; doi:10.3390/molecules15085595
Article

Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

1,2,* , 1, 1, 1, 1, Jr. 3 and 3
Received: 26 July 2010; in revised form: 12 August 2010 / Accepted: 12 August 2010 / Published: 13 August 2010
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Abstract: The first enantioselective syntheses of sulfur flavan-3-ol analogues 18 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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 AlCl3. The compounds were isolated in high chemical and optical purity.
Keywords: flavan-3-ols; 5,7-dideoxythiocatechin; 5,7-dideoxythioepicatechin; thiocatechin; thioepicatechin; asymmetric dihydroxylation flavan-3-ols; 5,7-dideoxythiocatechin; 5,7-dideoxythioepicatechin; thiocatechin; thioepicatechin; asymmetric dihydroxylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Sharma, P.K.; He, M.; Jurayj, J.; Gou, D.-M.; Lombardy, R.; Romanczy, L.J., Jr.; Schroeter, H. Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols. Molecules 2010, 15, 5595-5619.

AMA Style

Sharma PK, He M, Jurayj J, Gou D-M, Lombardy R, Romanczy LJ, Jr, Schroeter H. Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols. Molecules. 2010; 15(8):5595-5619.

Chicago/Turabian Style

Sharma, Pradeep K.; He, Min; Jurayj, Jurjus; Gou, Da-Ming; Lombardy, Richard; Romanczy, Leo J., Jr.; Schroeter, Hagen. 2010. "Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols." Molecules 15, no. 8: 5595-5619.



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