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Título

Arylacetic acid derivatization of 2,3- and internal erythro-squalene diols. Separation and absolute configuration determination

AutorAbad, José Luis; Camps Díez, Francisco
Palabras claveSqualene oxides
Squalene diols
Resolution
Enantiomers
Derivatization
Arylacetic acids
Fecha de publicación8-oct-2004
EditorElsevier
CitaciónTetrahedron 60(50): 11651-11663 (2004)
ResumenWe have studied a new approach for the resolution and absolute configuration determination of the enantiomers of squalene diols as intermediate precursors in the chemical synthesis of different squalene oxides (SOs); (3R)- and (3S)-2,3-SO, (6R,7R)- and (6S,7S)-6,7-SO, and (10R,11R)- and (10S,11S)-10,11-SO. Monoderivatization of the corresponding racemic squalene diol intermediates with pure stereoisomers of (S)-(+)-methoxyphenyl acetic acid ((S)-(+)-MPA), (S)-(+)-9-anthrylmethoxyacetic acid ((S)-(+)-9-AMA) and (S)-(+)-acetoxyphenylacetic acid ((S)-(+)-APA) afforded the diastereomeric esters which could be easily separated by column flash chromatography with silica gel. In addition, the absolute configuration for these diastereoisomers of the derivatized diols was advantageously inferred from 1H NMR data according to the models depicted for these derivatizing chiral agents. In order to demonstrate the absolute configuration assignment of the different stereoisomers, (S)-(+)-AMA showed the larger Δδ by 1H NMR, however, (S)-(+)-MPA esters were much more stable derivatives.
Descripción7 pages, 1 figure, 3 schemes.-- Printed version published Dec 6, 2004.
Versión del editorhttp://dx.doi.org/10.1016/j.tet.2004.09.059
URIhttp://hdl.handle.net/10261/18160
DOI10.1016/j.tet.2004.09.059
ISSN0040-4020
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