Total synthesis of the four enantiomerically pure diastereomers of 8-F(2t)-isoprostane.
Syntheses of the four enantiomerically pure diastereomers of 8-F(2t)-isoprostane (5-8) are described. The key to this approach was to prepare the racemic alcohol 9 in high diastereomeric purity and then resolve 9 by lipase-mediated acetylation to yield the enantiomerically pure alcohols 30 and 32.
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA. taberdf@udel.edu
D F
DF
Taber
Q
Q
Jiang
D015237:Dinoprost / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D028441:F2-Isoprostanes; D015394:Molecular Structure; D013057:Spectrum Analysis; D013237:Stereoisomerism
D028441:F2-Isoprostanes; C075750:8-epi-prostaglandin F2alpha; D015237:Dinoprost