Evidence for pi-Stacking as a Source of Stereocontrol in the Synthesis of the Core Pyranochromene Ring System common to Calyxin I, Calyxin J, and Epicalyxin J

Cakir S., Stokes S., Sygula A., Mead K. T.

JOURNAL OF ORGANIC CHEMISTRY, vol.74, no.19, pp.7529-7532, 2009 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 19
  • Publication Date: 2009
  • Doi Number: 10.1021/jo901436u
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.7529-7532

Abstract

A diastereoselective synthesis of the tetrahydropyrano-chromene ring system common to several natural product isolates of Alpinia blepharocalyx is reported. We have shown that a stereochemical preference exists for a syn configuration between the anomeric aryl substituents, representative of the C-7 and C-7' substituents in the natural products. Further, our results show that stereocontrol is under kinetic control, and calculations suggest that a favorable pi-stacking interaction may be the source of this stereocontrol.