Time Economical Total Synthesis of (-)-Oseltamivir

Yujiro Hayashi, Shin Ogasawara

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

A time economical 60 min total synthesis of (-)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.

Original languageEnglish
Pages (from-to)3426-3429
Number of pages4
JournalOrganic letters
Volume18
Issue number14
DOIs
Publication statusPublished - 2016 Jul 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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