Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines

Kottakota, S.K; Benton, M; Evangelopoulos, D; Guzman, J.D; Bhakta, S; McHugh, T.D; Gray, M; Groundwater, P.W; Marrs, E.C.L; Perry, J.D; Harburn, J.J

Abstract

The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.

Citation

Kottakota, S., Benton, M., Evangelopoulos, D., Guzman, J., Bhakta, S., McHugh, T., …Harburn, J. (2012). Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines. Organic Letters, 14(24), 6310-6313. https://doi.org/10.1021/ol303057a

• Journal Article Type: Article
• Publication Date: Dec 1, 2012
• Deposit Date: Dec 21, 2012
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 14
• Issue: 24
• Pages: 6310-6313
• DOI: https://doi.org/10.1021/ol303057a
• Public URL: https://durham-repository.worktribe.com/output/1469749