Total synthesis of nigellicine and nigeglanine hydrobromide.
[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.
Elliott
Eric L
EL
E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Bushell
Simon M
SM
Cavero
Marta
M
Tolan
Brian
B
Kelly
T Ross
TR
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
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D007191:Indazoles; C493028:nigeglanine; C508400:nigellicine