title: Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A.
abstract: The asymmetric aziridination of cyclic enones with N-tosyloxycarbamates, using N-neopentyl 1,2-diphenylethylenediamine as a catalyst, and its application to the formal total synthesis of (-)-agelastatin A, using a one-pot silylation-selenylation procedure and the regioselective aziridine-opening by an azide anion as key steps, are described.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Menjo
authors.forename: Akinari
authors.initials: A
authors.lastname: Hamajima
authors.forename: Neri
authors.initials: N
authors.lastname: Sasaki
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Hamada
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003959:Diamines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001388:Aziridines; D003959:Diamines; D007659:Ketones; D023303:Oxazolidinones; C464968:agelastatin A; C033132:aziridine