Prostaglandins and prostaglandin intermediates. XIV. Synthesis of rac-9α, 11α, 13α-trihydroxy- and rac-9α, 11α, 13β-Trihydroxy-5(Z)-prosten-15-ynoic Acid

Attempts to rearrange a β-hydroxy-alkyne with a secondary hydroxy group into an α,β-unsaturated ketone failed in the case of a potential prostaglandin intermediate. However, it was possible to convert this intermediate into 13-hydroxy-5(Z)-prosten-15-ynoic acids, which are interesting prostaglandin analogues with a modified alkyl side chain.