A facile synthesis of dragmacidin B and 2,5-bis(6'-bromo-3'-indolyl)piperazine.
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.
Miyake
F Y
FY
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
Yakushijin
K
K
Horne
D A
DA
D000818:Animals; D007211:Indoles / Q000138:chemical synthesis*; D008745:Methylation; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*
C415662:2,5-bis(6'-bromo-3'-indolyl)piperazine; D007211:Indoles; D010879:Piperazines; C415663:dragmacidin B