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The First Total Synthesis of Dragmacidin D

2002; American Chemical Society; Volume: 124; Issue: 44 Linguagem: Inglês

10.1021/ja027822b

1943-2984

Neil K. Garg, Richmond Sarpong, Brian M. Stoltz,

Chemical Synthesis and Analysis

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.