Synthesis of 2-Dimethylaminoimidazole Derivatives: A New Access to Indolyl-imidazole Alkaloids of Marine Origin.

Article abstract of DOI:10.1016/S0040-4039(00)92376-1

The first preparation of 2-dimethylaminoimidazole 1a, a structural feature of several marine products was undertaken and its reactivity investigated.The synthesis of natural alkaloids 5 and 12b was achieved by direct coupling of the easily accessible oxidized 2-dimethylaminoimidazoles 7 and 8 with indole-3-carboxaldehyde and indole respectively, demonstrating the usefulness of this approach for other structurally related natural products. Key Words: indolyl-imidazoles; alkaloids; aplysinopsin; 2-dimethylaminoimidazole; marine products.