1309575-65-2

Upstream product

• 1309575-64-1 (1S,3S,5R)-3-methoxy-8,8-di(methoxycarbonyl)-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 100-51-6 benzyl alcohol 

Downstream Products

• 823229-54-5 NPI-2077 
• 1309575-66-3 (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-67-4 (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-hydroxymethyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-76-5 (1S,3S,5R,8S)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-formyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-69-6 (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-68-5 (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-79-8 (1S,3R,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-78-7 (1S,3R,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)(hydroxy)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one 
• 1309575-70-9 (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone 
• 437742-34-2 salinosporamide A 

Relevant academic research and scientific papers

Total synthesis of (-)-salinosporamide A

A concise and stereoselective total synthesis of (-)-salinosporamide A (1), a potent inhibitor of the 20S proteasome that is in clinical development as an anticancer drug candidate, has been accomplished in 14 steps with 19% overall yield from 4-pentenoic acid. Our synthesis features a stereoselective alkylation utilizing a chiral auxiliary, formation of a pyrrolidine unit, and oxidation of the pyrrolidine to a γ-lactam. To demonstrate the scalability of our synthesis, (-)-salinosporamide A has been synthesized on a gram scale.