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

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

doi:10.1016/S0040-4020(97)01015-6

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

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	16287-16298
Number of pages	12
Journal	Tetrahedron
Volume	53
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4020(97)01015-6
Publication status	Published - 1997 Dec 1

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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AU - Chida, Noritaka

AU - Takeoka, Jun

AU - Ando, Kohji

AU - Tsutsumi, Noriko

AU - Ogawa, Seiichiro

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AB - 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.

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