Total synthesis of (+)-lactacystin from D-glucose

Noritaka Chida; Jun Takeoka; Noriko Tsutsumi; Seiichiro Ogawa

doi:10.1039/C39950000793

Total synthesis of (+)-lactacystin from D-glucose

Noritaka Chida, Jun Takeoka, Noriko Tsutsumi, Seiichiro Ogawa

Department of Applied Chemistry

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

54 Citations (Scopus)

Abstract

The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.

Original language	English
Pages (from-to)	793-794
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	7
DOIs	https://doi.org/10.1039/C39950000793
Publication status	Published - 1995 Dec 1

ASJC Scopus subject areas

Molecular Medicine

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title = "Total synthesis of (+)-lactacystin from D-glucose",

abstract = "The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.",

author = "Noritaka Chida and Jun Takeoka and Noriko Tsutsumi and Seiichiro Ogawa",

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AU - Takeoka, Jun

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AU - Ogawa, Seiichiro

PY - 1995/12/1

Y1 - 1995/12/1

N2 - The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.

AB - The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.

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Total synthesis of (+)-lactacystin from D-glucose

Abstract

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