title: Total synthesis of (-)-aspergilazine A.
abstract: The total synthesis of (-)-aspergilazine A, an alkaloid possessing a rare N1' to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1'-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F.
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors.forename: Emily M
authors.initials: EM
authors.lastname: Boyd
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001230:Aspergillus / Q000737:chemistry; D002384:Catalysis; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D008386:Marine Biology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004151:Dipeptides; D026121:Indole Alkaloids; D008024:Ligands; C505497:aspergillazine A; C000590722:brevianamide F; D010165:Palladium