A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

被引：0
|
作者：
J. K. Khalaf
A. Datta
机构：
[1] The University of Kansas,Department of Medicinal Chemistry
来源：
Amino Acids | 2008年 / 35卷
关键词：
Keywords: Non-proteinogenic amino acid – Sharpless asymmetric aminohydroxylation – Exhaustive oxidation – Orthogonally protected functional groups;
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摘要：
3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymmetric synthetic route to a strategically protected 3-hydroxyaspartic acid derivative in enantiopure form. The key steps in the synthesis involve, Sharpless asymmetric aminohydroxylation of commercially available trans-ethyl cinnamate, and, utilization of the phenyl group as a masked carboxylic acid synthon towards construction of the complete structural framework of the title compound.
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页码：507 / 510
页数：3
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