title: Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.
abstract: A total synthesis of the isoprostane (+/-)-8-epi-PGF(2)(alpha) ethyl ester (5) is described, based on the diastereoselective cyclization of alpha-diazo ketone 7. This ketone is assembled by aldol condensation between alpha-diazo ketone 8 and aldehyde 9. The sequential alpha-diazo ketone aldol/insertion described here offers a powerful new approach to cycloalkane construction.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.
authors.forename: Douglass F.
authors.initials: DF
authors.lastname: Taber
authors.forename: R. Jason
authors.initials: RJ
authors.lastname: Herr
authors.forename: D. Mark
authors.initials: DM
authors.lastname: Gleave