Issue 15, 1978

Novel synthesis of prostaglandin-E2 involving regioselective ring opening of a 2,3-endo-epoxybicyclo[3.2.0]heptan-6-one acetal with a mixed organocuprate reagent

Abstract

The epoxyacetal (2) is ring opened by appropriate organometallic reagents regioselectively to afford the acetals (15) and (17) in high yield; the acetal (15) was transformed into the prostaglandin-F2α precursor (4) in two steps, while (17) furnished the prostaglandin-E2 intermediate (24) in three steps.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1978, 662-664

Novel synthesis of prostaglandin-E2 involving regioselective ring opening of a 2,3-endo-epoxybicyclo[3.2.0]heptan-6-one acetal with a mixed organocuprate reagent

R. F. Newton, C. C. Howard, D. P. Reynolds, A. H. Wadsworth, N. M. Crossland and S. M. Roberts, J. Chem. Soc., Chem. Commun., 1978, 662 DOI: 10.1039/C39780000662

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