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A "shortcut" Mosher Ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A

Curran, DP and Sui, B (2009) A "shortcut" Mosher Ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A. Journal of the American Chemical Society, 131 (15). 5411 - 5413. ISSN 0002-7863

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Abstract

A "shortcut" of the advanced Mosher rule for use in assigning stereocenters in molecules with elements of local symmetry is proposed. A single Mosher ester is made, and the chemical shifts of pairs of resonances related by local symmetry are subtracted from each other (rather than from analogous resonances in the isomeric Mosher ester) to provide the configuration. Fluorous mixture synthesis is used to make a stereoisomer library of the four isomers of petrocortyne A. These samples and the derived Mosher esters are used to assign the (3S,14S) configuration to petrocortyne A and to validate both the standard and shortcut Mosher methods for use in the petrocortyne family of dialkynyl carbinols. © 2009 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Sui, B
Date: 22 April 2009
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 131
Number: 15
Page Range: 5411 - 5413
DOI or Unique Handle: 10.1021/ja900849f
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Esters; Fatty Alcohols--chemical synthesis; Fatty Alcohols--chemistry; Magnetic Resonance Spectroscopy--methods; Methods; Molecular Conformation; Stereoisomerism
Other ID: NLM NIHMS105988, NLM PMC2891898
PubMed Central ID: PMC2891898
PubMed ID: 19323551
Date Deposited: 21 Feb 2013 22:33
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/17380

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