A concise route to (+)-lactacystin

Hidenori Ooi; Norihisa Ishibashi; Yoshiharu Iwabuchi; Jun Ishihara; Susumi Hatakeyama

doi:10.1021/jo048817o

A concise route to (+)-lactacystin

J Org Chem. 2004 Oct 29;69(22):7765-8. doi: 10.1021/jo048817o.

Authors

Hidenori Ooi¹, Norihisa Ishibashi, Yoshiharu Iwabuchi, Jun Ishihara, Susumi Hatakeyama

Affiliation

¹ Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.

PMID: 15498013
DOI: 10.1021/jo048817o

Abstract

A facile chromatography-free route to Kang's intermediate for the synthesis of (+)-lactacystin, a potent proteasome inhibitor, has been developed starting with Brown's asymmetric crotylation of tert-butyl 5-formyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate, easily available from 2-amino-2-(hydroxymethyl)propane-1,3-diol (Tris).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcysteine / analogs & derivatives*
Acetylcysteine / chemical synthesis*
Carbamates / chemistry
Catalysis
Molecular Structure
Proteasome Inhibitors
Stereoisomerism
Tromethamine / chemistry*

Substances

Carbamates
Proteasome Inhibitors
Tromethamine
lactacystin
Acetylcysteine