Enantioselective Total Synthesis of Beraprost Using Organocatalyst

Shigenobu Umemiya, Daisuke Sakamoto, Genki Kawauchi, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

A convergent and enantioselective total synthesis of the most active isomer of beraprost was achieved in 17 pots. A unique tricyclic core in beraprost was synthesized efficiently by utilizing the asymmetric organocatalyst-mediated formal [3 + 2] cycloaddition reaction of succinaldehyde with nitroalkene as a key step. The synthesis of the optically active Horner-Wadsworth-Emmons reagent for the construction of the ω-side chain was also established by means of the enantioselective Michael reaction of crotonaldehyde with nitromethane catalyzed by the organocatalyst developed by our group.

Original languageEnglish
Pages (from-to)1112-1115
Number of pages4
JournalOrganic letters
Volume19
Issue number5
DOIs
Publication statusPublished - 2017 Mar 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective Total Synthesis of Beraprost Using Organocatalyst'. Together they form a unique fingerprint.

Cite this