Synthesis of tetranor-PGE1: A urinary metabolite of prostaglandins E1 and E2. Issue 22 (28th May 2020)

• Record Type: Journal Article
• Authors: Kimbrough, Jennifer R.; Jana, Somnath; Kim, Kwangho; Allweil, Alexander; Oates, John A.; Milne, Ginger L.; Sulikowski, Gary A.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 22(2020)
• Publication Date: 2020-05-28
• Subjects: Total synthesis -- Prostaglandins -- Synthesis strategy -- Heck reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151922
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 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. Abstract: Prostaglandin E2 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-PGE1 is described including a late stage incorporation of an isotopically labeled side-chain.