title: Total synthesis of nigellicine and nigeglanine hydrobromide.
abstract: [reaction: see text] The first syntheses of the pyridazinoindazolium alkaloids nigellicine and nigeglanine hydrobromide via a common intermediate are described. Ortho-lithiation/acylation and the direct amination of an isatin ring system are the key steps in the synthesis.
authors.affiliation: E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Eric L
authors.initials: EL
authors.lastname: Elliott
authors.forename: Simon M
authors.initials: SM
authors.lastname: Bushell
authors.forename: Marta
authors.initials: M
authors.lastname: Cavero
authors.forename: Brian
authors.initials: B
authors.lastname: Tolan
authors.forename: T Ross
authors.initials: TR
authors.lastname: Kelly
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007191:Indazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D031844:Nigella / Q000737:chemistry
chemical_list: D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D007191:Indazoles; C493028:nigeglanine; C508400:nigellicine