212772-68-4

Upstream product

• 20839-80-9 (4-methoxybenzylamino)acetic acid methyl ester 
• 50-00-0 formaldehyd 
• 212772-59-3 (R)-1-(4-Methoxy-benzyl)-4-methyl-4-methylsulfanyl-3,5-dioxo-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 212772-65-1 (1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione 
• 212772-70-8 (2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-1-(4-methoxy-benzyl)-4-methyl-4-methylsulfanyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 212772-63-9 (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 212772-69-5 (2R,3R,4R)-2-(2,2-Dimethyl-propionyloxymethyl)-3-hydroxy-1-(4-methoxy-benzyl)-4-methyl-4-methylsulfanyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 212772-72-0 (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 212772-61-7 (5R,4R,3R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-1-(4-methoxybenzyl)-3-methyl-3-methylsulfanyl-2-oxo-pyrrolidine-5-carboxylic acid methyl ester 
• 212772-62-8 (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 212772-64-0 (2R,3S,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 154226-60-5 omuralide 
• 133343-34-7 Lactacystin 
• 212772-60-6 (5R,4S,3R)-4-hydroxy-5-hydroxymethyl-1-(4-methoxybenzyl)-3-methyl-3-methylsulfanyl-2-oxo-pyrrolidine-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Formal synthesis of (+)-lactacystin from l-serine

A formal, stereocontrolled synthesis of lactacystin has been completed from t-Bu-O-l-serine, providing the key intermediate 13, also useful for the generation of a range of C-9 analogues.

A new synthetic approach to (+)-lactacystin based on radical cyclisation of enantiopure α-ethynyl substituted serine derivatives to 4-methylenepyrrolidinones

Treatment of the acetylenic bromoamide 42c, derived from the enantiopure α-amino alcohol 40, with Bu3SnH-AlBN results in an efficient 5-exo dig radical cyclisation to the 4-methylenepyrrolidinone 43/44 (2: 1). Cleavage of the alkene bond in 43/

Formal synthesis of (+)-lactacystin based on a novel radical cyclisation of an α-ethynyl substituted serine

A diastereoselective 5-exo-dig radical cyclisation of the bromoamide 7 produced from the enantiopure α-ethynyl substituted amino alcohol 5 led to the pyrrolidinone 8 (2:1 α:β epimers) in 70% yield. Oxidative cleavage of the alkene bond in 8, followed by a

An efficient and concise enantioselective total synthesis of lactacystin

A selective, irreversible inhibitor of proteasome function, lactacystin (1) is an important experimental tool in cell biology. An efficient and direct enantioselective synthesis of lactacystin proceeds via the intermediates shown below. This process allow