Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst

Genki Kawauchi, Shigenobu Umemiya, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

An enantioselective total synthesis of latanoprost was achieved. Its chiral cyclopentane core structure was constructed through an organocatalyst-mediated [3+2]-cycloaddition reaction, and chirality in the ω-side chain was generated by prolinate-anion-mediated α-aminoxylation of an aldehyde. Highly diastereoselective domino acetalization and an oxy-Michael reaction were key steps for the generation of C9 chirality.

Original languageEnglish
Pages (from-to)8409-8414
Number of pages6
JournalChemistry - A European Journal
Volume24
Issue number33
DOIs
Publication statusPublished - 2018 Jun 12

Keywords

  • asymmetric synthesis
  • cycloaddition
  • epimerization
  • organocatalysis
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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