The bromo-ketone (4) reacted with the cuprate reagent (2) to give the norbornanone (5). Two ways of converting the ketone (5) into the unsaturated lactone (8) were discovered. The lactone (8) was converted into the hydroxyaldehyde (9)en route to 9-deoxa-9,10-didehydroprostaglandin D2(10) and into prostaglandin A2(12)via the γ-lactone (11).
M. A. W. Finch, S. M. Roberts, G. T. Woolley and R. F. Newton, J. Chem. Soc., Perkin Trans. 1, 1981, 1725 DOI: 10.1039/P19810001725
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