Roxbin B is cuspinin: structural revision and total synthesis

J Org Chem. 2013 Jun 7;78(11):5410-7. doi: 10.1021/jo400562k. Epub 2013 May 20.

Abstract

Prompted by the outcome that the synthesized roxbin B was not identical to the natural roxbin B, the structural determination process and spectral data were re-examined, with the finding that roxbin B was very likely to be 1-O-galloyl-2,3-(R);4,6-(S)-bis-O-hexahydroxydiphenoyl-β-d-glucose (cuspinin). Because the (R)-axial chirality is rare in natural products when the hexahydroxydiphenoyl group bridges the 2- and 3-oxygens, the proposed structure of cuspinin was confirmed by the total synthesis, leading to the conclusion that roxbin B is the same as cuspinin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Hydrolyzable Tannins / chemical synthesis*
  • Hydrolyzable Tannins / chemistry*
  • Molecular Conformation
  • Molecular Structure

Substances

  • Biological Products
  • Hydrolyzable Tannins
  • roxbin B