title: Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine.
abstract: Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyamphimedine and amphimedine.
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds St, Auckland 1010, New Zealand.
authors.forename: Iman M
authors.initials: IM
authors.lastname: Khalil
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds St, Auckland 1010, New Zealand.
authors.forename: David
authors.initials: D
authors.lastname: Barker
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds St, Auckland 1010, New Zealand.
authors.forename: Brent R
authors.initials: BR
authors.lastname: Copp
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000166:Acridines; D000470:Alkaloids; D001688:Biological Products; D010618:Phenanthrolines; C429965:deoxyamphimedine; C475900:pyridoacridine; C475901:amphimedine