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Total Synthesis of Prostaglandin 15d-PGJ(2) and Investigation of its Effect on the Secretion of IL-6 and IL-12.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Egger Julian, Fischer Stefan, Bretscher Peter, Freigang Stefan, Kopf Manfred, Carreira Erick,
Project An apparatus for the real-time analysis of cellular metabolism
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Original article (peer-reviewed)

Journal Organic Letters
Volume (Issue) 17(17)
Page(s) 4340 - 4343
Title of proceedings Organic Letters
DOI 10.1021/acs.orglett.5b02181


An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.