Pot-Economical Total Synthesis of Clinprost

Nariyoshi Umekubo, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


The pot-economical synthesis of clinprost is reported, in which the core bicyclo[3.3.0]octenone structure was synthesized by two key steps: an asymmetric domino Michael/Michael reaction catalyzed by diphenylprolinol silyl ether and an intramolecular Horner-Wadsworth-Emmons reaction. The trisubstituted endocyclic alkene was selectively introduced by 1,4-reduction followed by trapping of the generated enolate with Tf2NPh and subsequent utilization of the Suzuki-Miyaura coupling reaction. Chiral, nonracemic clinprost was synthesized in seven pots with a 17% total yield and excellent enantioselectivity.

Original languageEnglish
Pages (from-to)9365-9370
Number of pages6
JournalOrganic Letters
Issue number23
Publication statusPublished - 2020 Dec 4


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