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Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester
Douglass F. Taber1, R. Jason Herr, D. Mark Gleave
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.
The Journal of Organic Chemistry
|January 10, 1997
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.