A potential route to neuroprostanes and isoprostanes: preparation of the four enantiomerically pure diastereomers of 13-F4t-neuroP.
We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F4t-neuroprostane.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Reddy
P Ganapati
PG
Arneson
Kyle O
KO
D003500:Cyclization; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
D028421:Isoprostanes; D020005:Propanols; C006463:allyl alcohol