1277168-71-4Relevant articles and documents
Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide
Fustero, Santos,Moscardó, Javier,Sánchez-Roselló, María,Flores, Sonia,Guerola, Marta,Pozo, Carlos Del
, p. 7412 - 7417 (2011)
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
Benlahrech, Meriem,Lahosa, Alejandro,Behloul, Cherif,Foubelo, Francisco,Yus, Miguel
, p. 1191 - 1202 (2019/07/31)
– 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.
