American Chemical Society
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Diastereoselective Synthesis of an Isoprostane: (±)-8-epi-PGF2α Ethyl Ester

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journal contribution
posted on 1997-01-10, 00:00 authored by Douglass F. Taber, R. Jason Herr, D. Mark Gleave
A total synthesis of the isoprostane (±)-8-epi-PGF2α ethyl ester (5) is described, based on the diastereoselective cyclization of α-diazo ketone 7. This ketone is assembled by aldol condensation between α-diazo ketone 8 and aldehyde 9. The sequential α-diazo ketone aldol/insertion described here offers a powerful new approach to cycloalkane construction.