168779-59-7

Upstream product

• 133-13-1 ethyl diethyl malonate 
• 10444-12-9 diethyl 2-(2-cyanoethyl)-2-ethylmalonate 
• 7033-83-2 ethyl 3-ethyl-2-oxopiperidine-3-carboxylate 

Downstream Products

• 849738-63-2 2-(1-benzenesulfonyl-3-{2-[3-(2-diazo-2-ethoxycarbonylacetyl)-3-ethyl-2-oxopiperidin-1-yl]-2-oxoethyl}-1H-indol-2-yl)acrylic acid methyl ester 
• 786704-02-7 2-diazo-3-[3-ethyl-2-oxo-1-(2-vinyl-benzoyl)-piperidin-3-yl]-3-oxo-propionic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of the pentacyclic skeleton of the aspidosperma alkaloids using rhodium carbenoids as reactive intermediates

A series of diazo amido keto esters prepared from N-alkenyl-substituted 3-carbalkoxy-2-piperidone derivatives was treated with rhodium(II) acetate. Attack of the amido carbonyl oxygen at the resultant rhodium carbenoid center produced a transient push-pull carbonyl ylide dipole which underwent an intramolecular dipolar cycloaddition reaction. A related annulation sequence was used to prepare the pentacyclic skeleton of the aspidosperma family of alkaloids. Synthesis of the required diazo imide was carried out from 3- carboxy-3-ethyl-2-piperidone and N-methyl-3-indoleacetic acid. Treatment of the diazo imide with rhodium(II) acetate afforded a transient 1,3-dipole which subsequently underwent cycloaddition across the indole π-bond. The resulting clycloadduct is the consequence of endo cycloaddition with respect to the dipole which is fully in accord with the lowest energy transition state. The clycloadduct was converted in three steps into desacetoxy-4-oxo- 6,7-dihydrovindorosine. The stereochemistry of the final product was established by a X-ray crystallographic study.

HETEROARYL COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

Sequential ruthenium catalysis for olefin isomerization and oxidation: Application to the synthesis of unusual amino acids

How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation reactions. The method enables enantioselective syntheses of challenging α-tri- and tetrasubstituted α-amino acids including an expedient total synthesis of the antiepileptic drug levetiracetam.