Synthesis of the major urinary metabolite of prostaglandin D2

Abstract

Starting from the Corey lactone (3), the total synthesis of a specific urinary metabolite of prostaglandin D₂, viz., (Z)-9α,11β-dihydroxy-15-oxo-2,3,18,19-tetranorprost-5-ene-1,20-dioic acid (1) and its 5E-isomer is described. The synthetic material was isolated in a tricyclic form as the corresponding hemiacetal lactone (2). The g.c.m.s. characteristics of the methyl ester, trimethylsilyl ether derivative of this compound were identical with those previously described for the same derivative of the 11β-tetranor metabolite of PGD₂.