Stereoselective total synthesis of (+)-lactacystin from D-glucose

Noritaka Chida, Jun Takeoka, Kohji Ando, Noriko Tsutsumi, Seiichiro Ogawa

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon with nitrogen in 1 was effectively constructed from D-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.

Original languageEnglish
Pages (from-to)16287-16298
Number of pages12
JournalTetrahedron
Volume53
Issue number48
DOIs
Publication statusPublished - 1997 Dec 1

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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