143771-07-7

Upstream product

• 20763-19-3 (methoxymethylene)triphenylphosphorane 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 86136-88-1 pent-4-enylcarbamic acid benzyl ester 
• 1000806-50-7 (E)-(6-benzyloxycarbonylamino)-2-hexenal 
• 67036-44-6 methyl (S)-2-(5-oxopyrrolidin-2-yl)acetate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 6216-63-3 N-Cbz-Prolinol 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 

Downstream Products

• 929020-29-1 (2S)-N-benzyloxycarbonyl-2-(2-hydroxy-propyl)-pyrrolidine 
• 143771-09-9 (R)-2-(4-Oxo-heptyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 929020-31-5 (2S)-N-cis-cinnamoyl-2-(2-hydroxy-propyl)-pyrrolidine 
• 929020-30-4 (2S)-N-trans-cinnamoyl-2-(2-hydroxy-propyl)-pyrrolidine 
• 143771-08-8 (S)-2-((E)-4-Oxo-hept-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric total syntheses of (R)-bgugaine and (R)-irnidine

An enantioselective total synthesis of (R)-bgugaine and the first enantioselective total synthesis of (R)-irnidine are reported. The key steps are the asymmetric ‘clip-cycle’ formation of the pyrrolidine ring in 94:6 e.r., which is common to both natural

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid

(Chemical Equation Presented) An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

First synthesis of Trans- and Cis-dendrochrysanines

Trans- and cis-dendrochrysanines (1 and 2), isolated from t he stems of Dendrobium chrysanthum Wall., were first synthesized from l-proline. The absolute configuration of 1 and 2 was established to be S by the syntheses.{A figure is presented}. Dendrochry

Synthesis of tetradentate bisamino-bisthiol complexes of oxorhenium(V) as structural mimics of steroids

Two tetradentate chelate systems have been synthesized in order to prepare metal complexes with oxorhenium(V) whose structures will mimic that of steroids. The chelate system with amide/amine/thioether/thiol donor sites failed to give a stable complex, bu

Enantioselective Synthesis of (5R,9R)-5-Propyl-octahydroindolizine

A versatile and practical synthesis of the dendrobatid alkaloid 167B is described using a chiral amino acid as starting material.