Total Synthesis Of Nature Product Roseophilin

Nature product Roseophilin was isolated from streptomyces griseoviridis by Seto et al. in 1992, exhibiting potent cylotoxicity against K562 human erythroid leukemia cells and KB human epidermoid carcinoma cells. Because of their special structure and important application, numerous methods to synthesize these compounds have been reported.In this thesis, N-tosylpyrrole was synthesized in high yield starting from commercially available pyrrole, which then underwent acylation, reduction, tandem acylation-Nazarov cyclization reaction for the construction of the cyclopenta[b]pyrrol moiety and a RCM reaction to form the 13-membered ring to give the target product. This was the simplest method (6 steps) developed at present for the construction of the macrocyclic core of (±)-Roseophilin. All the new structures were confirmed on the basis of1HNMR,13CNMR and HRMS.