Multistep Continuous-Flow Synthesis of (-)-Oseltamivir

Shin Ogasawara, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.

Original languageEnglish
Article numberss-2016-z0587-op
Pages (from-to)424-428
Number of pages5
JournalSynthesis (Germany)
Volume49
Issue number2
DOIs
Publication statusPublished - 2017 Jan 18

Keywords

  • Tamiflu
  • continuous flow
  • organocatalysis
  • time economy
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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