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RESEARCH PRODUCT
Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide
Sonia FloresCarlos Del PozoSantos FusteroMarta GuerolaMaría Sánchez-rosellóJavier Ruiz Moscardósubject
MyrtineLupinineQuinolizidineStereochemistryOrganocatalysisOrganic ChemistryEnantioselective synthesisEpiquinamideBiochemistryEpiquinamideCatalysischemistry.chemical_compoundLupininechemistryOrganocatalysisIntramolecular forceDrug DiscoveryOrganic chemistryQuinolizidine alkaloidsIntramolecular aza-Michael reactiondescription
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 Jorgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-09-01 |