Pot-Economical Total Synthesis of Clinprost

Nariyoshi Umekubo, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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
Volume22
Issue number23
DOIs
Publication statusPublished - 2020 Dec 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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