title: Aziridine-based concise synthesis of (±)-alstonerine.
abstract: A concise synthesis of the macroline-related alkaloid (±)-alstonerine is reported. Key steps are regioselective and stereospecific aziridine ring-opening using a sulfone-stabilised carbanion, Me3Al-mediated O → N-transacylation-elimination, intramolecular Michael reaction, and one-pot reduction-dehydration-Pictet-Spengler cyclisation.
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK. d.craig@imperial.ac.uk.
authors.forename: Donald
authors.initials: D
authors.lastname: Craig
authors.forename: Frederick W
authors.initials: FW
authors.lastname: Goldberg
authors.forename: Richard W
authors.initials: RW
authors.lastname: Pett
authors.forename: Niels T H
authors.initials: NT
authors.lastname: Tholen
authors.forename: Andrew J P
authors.initials: AJ
authors.lastname: White
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D026121:Indole Alkaloids; C510442:alstonerine; C033132:aziridine