A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid.
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.
Khalaf
J K
JK
Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
Datta
A
A
D000586:Amination; D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002934:Cinnamates / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
D002934:Cinnamates; C011274:3-hydroxyaspartic acid; D001224:Aspartic Acid; C451418:ethyl cinnamate