The first total synthesis of dragmacidin d.
The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product.
Garg
Neil K
NK
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 164-30, Pasadena, California 91125, USA.
Sarpong
Richmond
R
Stoltz
Brian M
BM
D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis; D010879:Piperazines / Q000138:chemical synthesis; D011161:Porifera / Q000737:chemistry
D004791:Enzyme Inhibitors; D026121:Indole Alkaloids; D007211:Indoles; D010879:Piperazines; C470335:dragmacidin D