Stereoselective synthesis of four stereoisomers of beta-methoxytyrosine, a component of callipeltin A.
Callipeltin A is a novel cyclic depsipeptide that selectively inhibits the cardiac sodium/calcium exchanger and is therefore of interest as a regulator of myocardial contractility. The stereochemistry of beta-methoxytyrosine, one of the amino acids contained within the marine natural product, could not be determined. In an effort to elucidate the stereochemistry of this moiety, a stereoselective synthesis of four stereoisomers of beta-methoxytyrosine from (S)- and (R)-serine was accomplished.
Hansen
Darren B
DB
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.
Wan
Xiaobo
X
Carroll
Patrick J
PJ
Joullié
Madeleine M
MM
D002384:Catalysis; D047630:Depsipeptides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D047630:Depsipeptides; D007202:Indicators and Reagents; C418139:callipeltin A; D014443:Tyrosine; C046013:4-methoxytyrosine