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

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