860453-75-4

Upstream product

• 78-84-2 isobutyraldehyde 
• 704910-29-2 methyl (4S,5R)-4,5-dihydro-2-(4-methoxyphenyl)-5-methyloxazole-4-carboxylate 

Downstream Products

• 860453-70-9 (2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-(iodomethyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 860453-71-0 (3R,3aS,7aR)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester 
• 860453-76-5 (2R,3S,4R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-4-(2-hydroxy-ethyl)-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 860453-69-6 (2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 857311-65-0 (2R,3S)-2-Acetyl-2-[acryloyl-(4-methoxy-benzyl)-amino]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid methyl ester 
• 860453-73-2 (2R,3S,4R)-4-(2-Chloro-ethyl)-3-hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide 
• 860453-68-5 (2R,3S)-2-Acetyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzylamino)-4-methyl-pentanoic acid methyl ester 
• 860453-67-4 (4S,5R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition

A short and highly stereocontrolled synthesis of the potent proteasome inhibitor 3 from the (S)-threonine-derived oxazoline 4 has been developed. The synthetic sequence is summarized in Scheme 1. Aldol coupling of the zinc enolate of 4 with isobutyraldehyde and subsequent silylation provided the TBS ether 5 diastereoselectively (10:1). Reductive cleavage of the oxazoline ring of 5 followed by Swern oxidation of the resulting amino alcohol afforded amino ketone 6, converted further by N-acylation to the acrylamide 7, whose structure was confirmed by X-ray crystallographic analysis. Acrylamide 7 was cyclized to 8 by a novel application of the Kulinkovich Ti(II)-cyclopentene complex. Silylation of 8 to 9 and radical cyclization at low temperature produced the bicyclic lactam 10 with complete control of all stereocenters. Hydroxy desilylation and N-deprotection of 10 gave the dihydroxy ester 11, which was converted to 3 by a novel three-step sequence: (1) demethylation with [Me2AlTeMe]2, (2) combined β-lactonization and chlorination, and (3) desilylation to effect cleavage of the TBS ether. Copyright