Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.
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.
Taber
Douglass F.
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.
Herr
R. Jason
RJ
Gleave
D. Mark
DM