Asymmetric Synthesis of Corey Lactone and Latanoprost

Nariyoshi Umekubo, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Corey lactone was synthesized in a single pot within 152 minutes in a 50 % overall yield via pot and time economical manner. Latanoprost, an antiglaucoma blockbuster drug, was also synthesized via seven pot reaction with five purifications in a 25 % total yield. One of the key reactions is asymmetric domino Michael/Michael reaction, formal [3+2] cycloaddition reaction, of 3-(dimethylphenylsilyl)propenal and ethyl 4-oxo-2-pentenoate, catalyzed by diphenylprolinol silyl ether, which constructed the core substituted cyclopentanone derivative with nearly optically pure form.

Original languageEnglish
Pages (from-to)6221-6227
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number39
DOIs
Publication statusPublished - 2020 Oct 22

Keywords

  • Domino reactions
  • One-pot reaction
  • Organocatalysis
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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