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, SIDIKA; Stokes, Sean; Sygula, Andrzej; Mead, Keith

doi:10.1021/jo901436u

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

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

JOURNAL OF ORGANIC CHEMISTRY, vol.74, no.19, pp.7529-7532, 2009 (Journal Indexed in SCI)

Publication Type: Article / Article
Volume: 74 Issue: 19
Publication Date: 2009
Doi Number: 10.1021/jo901436u
Title of Journal : JOURNAL OF ORGANIC CHEMISTRY
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.