1277168-71-4

Upstream product

• 1191-30-6 5-bromopentanal 
• 14660-52-7 ethyl 5-bromovalerate 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 351410-32-7 (R)-2-(1-(tert-butoxycarbonyl)piperidin-2-yl) acetic acid 
• 813433-73-7 (R)-2-methoxycarbonylmethylpiperidine-1-carboxylic acid tert-butyl ester 
• 725250-71-5 (1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester 
• 26892-59-1 epilupininic acid 
• 1334295-34-9 (R)-tert-butyl 2-[(R)-1-(methoxycarbonyl)-4-hydroxybutyl]piperidine-1-carboxylate 
• 1000806-51-8 (E)-(7-tert-butoxycarbonylamino)-2-heptenal 

Relevant academic research and scientific papers

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by J?rgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner.

Highly convergent straightforward stereoselective synthesis of (+)-C(9a)-epiepiquinamide

– The total synthesis of (+)-C(9a)-epiepiquinamide has been achieved starting from ethyl 5-bromopentanoate, (RS)-tert-butanesulfinamide, nitromethane, ethyl acrylate and acetic anhydride. The diastereoselective coupling of ethyl 4-nitrobutanoate and a chiral N-tert-butanesulfinyl imine, along with a double cyclization involving a primary amine through an intramolecular N-alkylation and lactam formation, are key steps of this synthesis.