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

Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

1,2,* , 1, 1, 1, 1, Jr. 3 and 3
1 Chemical Process Research & Development and Analytical Development, Johnson Matthey Pharmaceutical Materials Inc., 25 Patton Road, Devens, MA 01434, USA 2 Chemical Process R&D and CMC Regulatory, ARIAD Pharmaceuticals Inc., Cambridge, MA 02139, USA 3 MARS Incorporated, 6885 Elm Street, McLean, VA 22101, USA
* Author to whom correspondence should be addressed.
Received: 26 July 2010 / Revised: 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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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syntheses of sulfur flavan-3-ol analogues 18 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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 (CC BY 3.0).

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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.

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