title: A facile synthesis of dragmacidin B and 2,5-bis(6'-bromo-3'-indolyl)piperazine.
abstract: A short synthesis of dragmacidin B (1), 2,5-bis(6'-bromo-3'-indolyl)piperazine (2), and corresponding didebromo analogues 8 and 9 is described. The key steps involve the dimerization of oxotryptamines 4 and 11 to give bis(indolyl)pyrazines 5 and 12, which upon selective reduction and reductive methylation with sodium cyanoborohydride afforded the requisite piperazine natural products.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
authors.forename: F Y
authors.initials: FY
authors.lastname: Miyake
authors.forename: K
authors.initials: K
authors.lastname: Yakushijin
authors.forename: D A
authors.initials: DA
authors.lastname: Horne
mesh_terms: D000818:Animals; D007211:Indoles / Q000138:chemical synthesis*; D008745:Methylation; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*
chemical_list: C415662:2,5-bis(6'-bromo-3'-indolyl)piperazine; D007211:Indoles; D010879:Piperazines; C415663:dragmacidin B