704910-37-2

Upstream product

• 704910-34-9 methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde 
• 704910-33-8 methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate 
• 1027961-34-7 (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 704910-36-1 (2R,3S)-2-Benzyloxymethyl-3-(bromomethyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 857681-75-5 (3R,3aS,7aR)-3-((S)-1-Hydroxy-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 
• 857681-76-6 (2R,3S,4R)-3-Hydroxy-4-(2-hydroxy-ethyl)-2-[(S)-1-(isopropyl-dimethyl-silanyloxy)-2-methyl-propyl]-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 857681-81-3 (3R,3aS,7aR)-3-[(S)-1-(Isopropyl-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 
• 704910-38-3 (3S,3aS,7aR)-3-Formyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester 
• 1367878-74-7 (1R,4R,5S)-4-(2-chloroethyl)-2-(4-methoxybenzyl)-5-methyl-1-((S)-4,4,4-trifluoro-1-hydroxybutyl)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione 
• 1367878-73-6 (2R,3S,4R)-methyl 3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxo-2-((S)-4,4,4-trifluoro-1-hydroxybutyl)pyrrolidine-2-carboxylate 
• 1367878-72-5 (4aR,7R,7aS)-methyl 6-(4-methoxybenzyl)-2,2,7a-trimethyl-5-oxo-7-((S)-4,4,4-trifluoro-1-hydroxybutyl)octahydro-[1,2]oxasilino[5,6-c]pyrrole-7-carboxylate 
• 1367878-71-4 (1R,4R,5S)-4-(2-chloroethyl)-1-((R)-2,2-difluoro-1-hydroxybutyl)-2-(4-methoxybenzyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione 
• 1367878-70-3 (1R,4R,5S)-1-((R)-2,2-difluoro-1-hydroxybutyl)-4-(2-hydroxyethyl)-2-(4-methoxybenzyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione 
• 1367878-69-0 (2R,3S,4R)-methyl 2-((R)-2,2-difluoro-1-hydroxybutyl)-3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxopyrrolidine-2-carboxylate 
• 1367878-65-6 (4aR,7R,7aS)-methyl 7-((R)-2,2-difluoro-1-hydroxybut-3-en-1-yl)-6-(4-methoxybenzyl)-2,2,7a-trimethyl-5-oxooctahydro-[1,2]oxasilino[5,6-c]pyrrole-7-carboxylate 
• 1383921-55-8 C₂₀H₂₃F₂NO₆ 
• 1367878-68-9 (1R,4R,5S)-4-(2-chloroethyl)-1-((R)-2,2-difluoro-1-hydroxybut-3-en-1-yl)-2-(4-methoxybenzyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione 
• 704910-39-4 (3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

New synthetic route for the enantioselective total synthesis of salinosporamide A and biologically active analogues

(Chemical Equation Presented) A total synthesis of the salinosporamide analogue 3 is described that starts with the novel cyclization 4 → 5.

ANALOGS OF SALINOSPORAMIDE A

Disclosed herein are analogs of Salinosporamide A, having the Formulae Ia - IVa as follows: [insert chemical formula here] Like Salinosporamide A, the compounds of the present invention will inhibit the proteasome, an intracellular enzyme complex that destroys proteins the cell no longer needs. Without the proteasome, proteins would build up and clog cellular machinery. Fast-growing cancer cells make especially heavy use of the proteasome, so thwarting its action is a compelling drug strategy.

Simple stereocontrolled synthesis of salinosporamide A

A simple and effective stereocontrolled synthesis of salinosporamide A (1) has been developed which follows the pathway outlined in the Figure. The process, the first total synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. In addition to the method of Scheme I, the present invention also includes several novel synthetic intermediate compounds, several intermediate steps of the preferred synthetic process; and the uses of these compounds in the preparation of synthetic derivatives of the compound Salinosporamide A. Salinosporamide A is of special interest as a synthetic target because of its protein in vitro cytotoxic activity against many tumor cell lines (IC50 values of 10 nM or less).

A simple stereocontrolled synthesis of salinosporamide A

A simple and effective stereocontrolled synthesis of salinosporamide A has been developed. This process, the first synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. Salinosporamide A was of special interest as a synthetic target because of its potent in vitro cytotoxic activity against many tumor cell lines (IC50 values of 10 nM or less). Copyright