The synthesis of a combinatorial library using a tambjamine natural product template

The first demonstration of a parallel solution-phase synthesis using a tamb jamine natural product template is reported. Isolation of the salts of tamb jamines C (1), E (2) and F (3) from the Great Barrier Reef ascidian Sigilli na signifera, followed by base hydrolysis, produced the known metabolite 4- methoxy-2-(1H-pyrrol-2'-yl)-1H-pyrrole-5-carbaldehyde (4). This aldehyde wa s subsequently used in a one-step synthesis to generate an enamine library. A simple liquid-liquid partitioning scheme was employed for purification a nd provided 10 tambjamine analogues in high purity.