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

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

Research output: Contribution to journalArticle

63 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

Fingerprint

Lactams
Nerve Growth Factors
Nitrogen
Carbon
Amino Acids
Glucose
trichloroacetamide
lactacystin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective total synthesis of (+)-lactacystin from D-glucose. / Chida, Noritaka; Takeoka, Jun; Ando, Kohji; Tsutsumi, Noriko; Ogawa, Seiichiro.

In: Tetrahedron, Vol. 53, No. 48, 01.12.1997, p. 16287-16298.

Research output: Contribution to journalArticle

Chida, N, Takeoka, J, Ando, K, Tsutsumi, N & Ogawa, S 1997, 'Stereoselective total synthesis of (+)-lactacystin from D-glucose', Tetrahedron, vol. 53, no. 48, pp. 16287-16298. https://doi.org/10.1016/S0040-4020(97)01015-6
Chida, Noritaka ; Takeoka, Jun ; Ando, Kohji ; Tsutsumi, Noriko ; Ogawa, Seiichiro. / Stereoselective total synthesis of (+)-lactacystin from D-glucose. In: Tetrahedron. 1997 ; Vol. 53, No. 48. pp. 16287-16298.
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