10444-12-9

Upstream product

• 107-13-1 acrylonitrile 
• 133-13-1 ethyl diethyl malonate 
• 105-53-3 diethyl malonate 
• 17216-62-5 diethyl 2-(2-cyanoethyl)malonate 
• 75-03-6 ethyl iodide 

Downstream Products

• 86827-03-4 3-Ethyl-3-(2-oxo-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 168779-59-7 3-ethyl-2-oxo-piperidine-3-carboxylic acid 

Relevant academic research and scientific papers

Total synthesis of quebrachamine through macrolactamization

The total synthesis of quebrachamine was achieved through the macrolactamization of cis-2-alkenylated indole 17, which was prepared by a Sonogashira reaction between indole 5b and piperidine 11 followed by cis-hydrogenation. We found that stoichiometric c

A Concise Enantioselective Total Synthesis of (?)-Deoxoapodine

We have established a highly convergent 10-step route for the total synthesis of (?)-deoxoapodine, which is a hexacyclic aspidosperma alkaloid. The quaternary C5 center of the characteristic tetrahydrofuran ring was constructed by a chiral-phosphoric-acid

Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids

The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.

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.

Synthesis of new deazatetrahydropterins as potential NO synthase modulators

As part of our research on NO synthase modulators, a series of deazatetrahydropterins were synthesized and their effects were assessed. In this paper, we describe the synthesis of new substituted (especially at the 4a position) 2-amino-4-hydroxy-3,4,4a,5,6,7-hexahydropyrido[2,3-d]pyrimidines. These compounds showed no interesting pharmacological activity. Elsevier.