Preparing functional bis(indole) pyrazine by stepwise cross-coupling reactions: an efficient method to construct the skeleton of dragmacidin D.
A direct approach for selective construction of properly substituted bis(indole) pyrazine, the skeleton of a marine alkaloid dragmacidin D, has been developed. The key steps involved the regioselective introduction of two indole units, using the palladium(0)-catalyzed Suzuki and the Stille cross-coupling reactions sequentially.
Yang
Cai-Guang
CG
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China.
Liu
Gang
G
Jiang
Biao
B
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010165:Palladium / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis*
D000470:Alkaloids; D006842:Hydrocarbons, Brominated; D026121:Indole Alkaloids; D007211:Indoles; D010879:Piperazines; D011719:Pyrazines; C470335:dragmacidin D; D010165:Palladium