A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate

Yuko Kobayashi, Yoshiji Takemoto, Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

Abstract

The title synthesis could be accomplished by featuring the [2+2]-cycloaddition reaction of a chiral imine with benzyloxyketene, alcoholysis of the formed 2-azetidinone derivative, and reductive removal of the mandelate-derived benzylic oxygen by way of a 2-oxazolidone derivative.

Original languageEnglish
Pages (from-to)3031-3034
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number21
DOIs
Publication statusPublished - 1990
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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