Effective stereoselective total synthesis of 16,16-dimethyl prostaglandin E2

Ana Rodríguez, Miguel Nomen, Bernd W. Spur, Jean Jacques Godfroid

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The first stereoselective synthesis of the specific EP1 receptor agonist, 16,16-dimethyl prostaglandin E2 1, is described. The key- intermediate 3 was obtained from the E-allyl alcohol 6 via Sharpless epoxidation followed by stereospecific transformations to the γ-iodo vinyl compound 3. Two component coupling of 2 and 3, using the dilithiocyanocuprate technology, gave the 1,4-addition product. Mild desilylation and enzymatic ester cleavage produced the optically pure prostaglandin 1 in high yield.

Original languageEnglish (US)
Pages (from-to)279-282
Number of pages4
JournalArchiv der Pharmazie
Volume331
Issue number9
DOIs
StatePublished - Sep 1998

All Science Journal Classification (ASJC) codes

  • Pharmaceutical Science
  • Drug Discovery

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