title: Synthesis of N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((-)-julocrotine).
abstract: The total synthesis of (-)-julocrotine (1) starting from l-glutamic acid in 41% overall yield is described. The methodology utilizes protection, deprotection, and regioselection (carbonyl differentiation via oxazolidinone) protocols, and glutarimide ring formation is the key step.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina , Florianópolis, SC 88040-900, Brazil.
authors.forename: Luciano L
authors.initials: LL
authors.lastname: Silva
authors.forename: Antonio C
authors.initials: AC
authors.lastname: Joussef
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018698:Glutamic Acid / Q000737:chemistry*; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010881:Piperidones; D018698:Glutamic Acid; C428864:julocrotine