Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.
The nonproteinogenic amino acid (2R,3R)-beta-methoxytyrosine, a constituent of several cyclic depsipeptide natural products, was synthesized in protected form (8) from a readily available cinnamate ester in four steps and 62% overall yield with a greater than 28:1 er and 19:1 dr. This method provides a highly efficient, enantio- and diastereoselective synthesis of an important amino acid.
Department of Chemistry and Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
David C
DC
Cranfill
Mark A
MA
Lipton
D002934:Cinnamates / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C524009:(R,R)-beta-methoxytyrosine; D002934:Cinnamates; D047630:Depsipeptides; D004952:Esters; D014443:Tyrosine