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

A diastereoselective synthesis of the tetrahydropyranochromene 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...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-10, Vol.74 (19), p.7529-7532
Main Authors: Cakir, Sidika Polat, Stokes, Sean, Sygula, Andrzej, Mead, Keith T
Format: Article
Language:English
Subjects:
Alpinia - chemistry
Biological and medical sciences
Chemistry
Cyclization
Diarylheptanoids - chemical synthesis
Diarylheptanoids - chemistry
Diarylheptanoids - isolation & purification
Exact sciences and technology
General pharmacology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Kinetics and mechanisms
Medical sciences
Molecular Structure
Organic chemistry
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
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Summary:A diastereoselective synthesis of the tetrahydropyranochromene 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 π-stacking interaction may be the source of this stereocontrol.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901436u