Synthesis of tetranor-PGE1: A urinary metabolite of prostaglandins E1 and E2.

• Chemical synthesis of prostaglandin E2 metabolite "tetranor PGE1". • Heck coupling with acrolein diethyl acetal leads to an ester. • Cuprate conjugate addition to a 2-substited-5-alkoxycylopentenone. • Deuterium labeling affords a standard for a prostaglandin urinary metabolite. Prostaglandin E 2 is produced in response to inflammation, often associated with human disease. As prostaglandins are rapidly metabolized, quantification of end urinary metabolites depend on chemical synthesis of isotopically labeled standards to support metabolite quantification. A concise synthesis of tetranor-PGE 1 is described including a late stage incorporation of an isotopically labeled side-chain. [ABSTRACT FROM AUTHOR]