Enantioselctive syntheses of sulfur analogues of flavan-3-Ols

Molecules. 2010 Aug 13;15(8):5595-619. doi: 10.3390/molecules15085595.


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syntheses of sulfur flavan-3-ol analogues 1-8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom.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

MeSH terms

  • Cyclization
  • Flavonoids / chemical synthesis*
  • Flavonoids / chemistry*
  • Rotation
  • Stereoisomerism
  • Sulfur Compounds / chemical synthesis*
  • Sulfur Compounds / chemistry*


  • Flavonoids
  • Sulfur Compounds
  • flavan-3-ol