Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester

Douglass F. Taber; R. Jason Herr; D. Mark Gleave

doi:10.1021/jo9616365

Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester

J Org Chem. 1997 Jan 10;62(1):194-198. doi: 10.1021/jo9616365.

Authors

Douglass F. Taber¹, R. Jason Herr, D. Mark Gleave

Affiliation

¹ Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.

PMID: 11671381
DOI: 10.1021/jo9616365

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.