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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.

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.

SUBMITTER: Curran DP

PROVIDER: S-EPMC2891898 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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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 Dennis P DP Sui Bin B

Journal of the American Chemical Society 20090401 15

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 deriv ...[more]

PMID: 19323551

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