704910-45-2

Upstream product

• 2441-97-6 3-chloro-cyclohexene 
• 7440-66-6 zinc 
• 1165952-91-9 cyclohexa-1,3-diene 
• 112520-99-7 tributyl(cyclohex-2-en-1-yl)stannane 
• 7646-85-7 zinc(II) chloride 

Downstream Products

• 1064062-07-2 (4S)-4-{(S)-[(S)-cyclohex-2-enyl](hydroxy)methyl}-4-{[(2-methoxyethoxy)methoxy]methyl}-3-(4-methoxybenzyl)oxazolidin-2-one 
• 1039750-76-9 (S)-2-methyl-propane-2-sulfinic acid [(S)-1-((S)-cyclohex-2-enyl)-1-phenylpropyl]amide 
• 1039750-75-8 (S)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-phenyl)-1-((S)-cyclohex-2-enyl)ethyl]amide 
• 1039750-74-7 (S)-2-methyl-propane-2-sulfinic acid [(S)-1-((S)-cyclohex-2-enyl)-1-phenylethyl]amide 
• 1039750-73-6 (S)-2-methyl-propane-2-sulfinic acid [(S)-((S)-cyclohex-2-enyl)-(furan-2-yl)methyl]amide 
• 1039750-72-5 (S)-2-methyl-propane-2-sulfinic acid [(R)-1-((S)-cyclohex-2-enyl)propyl]amide 
• 1039750-71-4 (S)-2-methyl-propane-2-sulfinic acid [(R)-cyclohexyl-((S)-cyclohex-2-enyl)methyl]amide 
• 1039750-70-3 (S)-2-methyl-propane-2-sulfinic acid [(S)-(4-fluoro-2-bromo-phenyl)-((S)-cyclohex-2-enyl)methyl]amide 
• 1039750-69-0 (S)-2-methyl-propane-2-sulfinic acid [(S)-(4-methoxy-phenyl)-((S)-cyclohex-2-enyl)methyl]amide 
• 1039750-68-9 (S)-2-methyl-propane-2-sulfinic acid [(S)-(4-methyl-phenyl)-((S)-cyclohex-2-enyl)methyl]amide 
• 1039750-67-8 (S)-2-methyl-propane-2-sulfinic acid [(S)-((S)-cyclohex-2-enyl)-(4-fluoro-phenyl)methyl]amide 
• 1039750-66-7 (S)-2-methyl-propane-2-sulfinic acid [(S)-(4-bromo-phenyl)-((S)-cyclohex-2-enyl)methyl]amide 
• 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

PROTEASOME INHIBITING ?-LACTAM PRODRUGS USEFUL FOR THE TREATMENT OF CANCER AND NEURODEGENERATIVE DISORDERS

The present invention relates generally to proteasome inhibiting β-lactam compounds useful for the treatment of cancer and neurodegenerative disorders. The invention also provides pharmaceutical compositions and extended release formulations of said compounds, and medical uses of said compounds and/or pharmaceutical compositions to treat cancer and neurodegenerative disorders.

Highly diastereoselective synthesis of homoallylic alcohols bearing adjacent quaternary centers using substituted allylic zinc reagents

Staring from readily available polysubstituted allylic chlorides, a range of polysubstituted allylic zinc chlorides were obtained using a LiCl-mediated zinc dust insertion in 55-84% yield. A highly diastereoselective synthesis of homoallylic alcohols bear

TOTAL SYNTHESIS OF SALINOSPORAMIDE A AND ANALOGS THEREOF

The present invention relates to certain compounds and to methods for the preparation of certain compounds that can be used in the fields of chemistry and medicine. Specifically, described herein are methods for the preparation of various compounds and intermediates, and the compounds and intermediates themselves. More specifically, described herein are methods for synthesizing Salinosporamide A and its analogs from a compound of formula (V).

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.

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).