Synthesis of a Human Urinary Metabolite of Prostaglandin D2

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 ally...

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Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (24), p.10048-10051
Main Authors: Kimbrough, Jennifer R, Austin, Zachary, Milne, Ginger L, Sulikowski, Gary A
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03983