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Updated: Oct 3, 2026

Prostaglandin Extraction and Analysis in Caenorhabditis elegans
Published on: June 25, 2013
Synthesis of a Human Urinary Metabolite of Prostaglandin D2
Jennifer R Kimbrough1, Zachary Austin1, Ginger L Milne2,3
1Department of Chemistry , Vanderbilt University , Nashville , Tennessee 37232 , United States.
Abstract:
A chemical synthesis of the major human metabolite of prostaglandin D2, tricyclic-PGDM, is described. The synthetic route starts from iodocyclopentenone 1 (available from cyclopentadiene in 6 steps) and requires 13 synthetic transformations. The synthetic route takes advantage of a contrasteric allylation to establish the 1,2-cis relationship between the ring hydroxyl group and side chain. A second key sequence is the application of Fu's copper-catalyzed C-H insertion of a diazoacetate followed by an alkyne semihydrogenation to introduce the unsaturated side chain.
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