856682-04-7

Upstream product

• 856682-13-8 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester 
• 856681-99-7 (3S,7S,7aR)-3-Phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 856682-00-3 (3S,6R,7R,7aR)-6-(2-Benzyloxy-ethyl)-3-phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 856682-02-5 Carbonic acid (2R,3R,4R)-4-(2-benzyloxy-ethyl)-2-hydroxymethyl-5-oxo-pyrrolidin-3-ylmethyl ester ethyl ester 
• 856682-01-4 (3S,6R,7R,7aR)-6-(2-Benzyloxy-ethyl)-7-hydroxymethyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 856682-12-7 3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester 
• 856682-03-6 3-(2-benzyloxy-ethyl)-2-ethoxy-6-oxo-3a,4-dihydro-3H-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester 
• 856682-11-6 (2R,3R,4R)-4-(2-Benzyloxy-ethyl)-3-ethoxycarbonyloxymethyl-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 856681-96-4 4-(2-benzyloxy-ethyl)-5-ethoxy-3-ethoxycarbonyloxymethyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid tert-butyl ester 
• 856682-10-5 Carbonic acid (3S,6R,7R,7aR)-6-(2-benzyloxy-ethyl)-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-7-ylmethyl ester ethyl ester 
• 118867-99-5 (2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>oct-6-en-8-one 
• 15960-79-9 di-tert-butyl 2-bromomalonate 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 856681-97-5 (2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester 
• 856682-06-9 (2S,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-3-methylene-5-oxo-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester 
• 856682-05-8 (2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester 
• 915315-28-5 (2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Diastereoselective synthesis of fused lactone-pyrrolidinones; Application to a formal synthesis of (-)-salinosporamide a

A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.

SYNTHESIS OF SALINOSPORAMIDE A AND ANALOGUES THEREOF

A novel synthesis of salinosporamide A is provided. Salinospoamide A as well as structurally related natural products, omuralide and lactacystin, have been shown to be proteasome inhibitors. Therefore, these compounds as well as analogues of these natural products may be useful in the treatment of proliferative diseases such as cancer, autoimmune diseases, diabetic retinopathy, etc. The invention provides for the synthesis of salinosporamide A as well as analogs thereof using a convenient point for derivatization of the bicyclic core. Pharmaceutical compositions and method of using the inventive compounds are also provided.

Total synthesis of salinosporamide A

Total synthesis of potent proteasome inhibitor salinosporamide A (1) has been accomplished, which features strictly substrate-controlled operations starting with the only chiral center of (R)-pyroglutamic acid. The consecutive quaternary carbons within 1 have been efficiently constructed by manipulation of two intramolecular reactions: (1) carbonate-mediated internal acylation of imidate ester (4 → 14) and (2) selenocyclization of aldehyde to exocyclic methylene group (5 → 18). Copyright