Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

Molecules

Pradeep K. Sharma¹  Min He¹  Jurjus Jurayj¹  Da-Ming Gou¹  Richard Lombardy¹  Leo J. Romanczy¹ 

[1] ¹Chemical Process Research & Development and Analytical Development, Johnson Matthey Pharmaceutical Materials Inc., 25 Patton Road, Devens, MA 01434, USA ²Chemical Process R&D and CMC Regulatory, ARIAD Pharmaceuticals Inc., Cambridge, MA 02139, USA ³MARS Incorporated, 6885 Elm Street, McLean, VA 22101, USA

关键词: flavan-3-ols;    5;    7-dideoxythiocatechin;    5;    7-dideoxythioepicatechin;    thiocatechin;    thioepicatechin;    asymmetric dihydroxylation;   

DOI  :  10.3390/molecules15085595

来源: mdpi

【 摘 要 】

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syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.