176541-56-3Relevant academic research and scientific papers
Total synthesis of (+)-lactacystin
Nagamitsu, Tohru,Sunazuka, Toshiaki,Tanaka, Haruo,Omura, Satoshi,Sprengeler, Paul A.,Smith III, Amos B.
, p. 3584 - 3590 (2007/10/03)
A total synthesis of the novel neurotrophic agent (+)-lactacystin (1) has been achieved in 11 steps and 14% overall yield from (2R,3S)-3-hydroxyleucine [(+)-16]. The construction and bioassay of several active analogs are also described. A new asymmetric approach furnished the four stereoisomers of 3-hydroxyleucine, as required starting materials in high overall yield and enantiomeric purity.
An efficient asymmetric synthesis of the four stereoisomers of 3-hydroxyleucine
Sunazuka, Toshiaki,Nagamitsu, Tohru,Tanaka, Haruo,Omura, Satoshi,Sprengeler, Paul A.,Smith III, Amos B.
, p. 4447 - 4448 (2007/10/02)
The four stereoisomers of 3-hydroxyleucine have been prepared in high overall yield and enantiomeric purity. Key steps include Sharpless asymmetric epoxidation, benzyl isocyanate-induced epoxide opening, and epimerization of an intermediate oxazolidinone ester.
