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Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols
Chemical Process Research & Development and Analytical Development, Johnson Matthey Pharmaceutical Materials Inc., 25 Patton Road, Devens, MA 01434, USA
Chemical Process R&D and CMC Regulatory, ARIAD Pharmaceuticals Inc., Cambridge, MA 02139, USA
MARS Incorporated, 6885 Elm Street, McLean, VA 22101, USA
* Author to whom correspondence should be addressed.
Received: 26 July 2010; in revised form: 12 August 2010 / Accepted: 12 August 2010 / Published: 13 August 2010
Abstract: 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syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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 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
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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.
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.
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.