Organic Letters 2012-12-21

Versatile routes to marine sponge metabolites through benzylidene rhodanines.

Suresh K Kottakota, Mathew Benton, Dimitrios Evangelopoulos, Juan D Guzman, Sanjib Bhakta, Timothy D McHugh, Mark Gray, Paul W Groundwater, Emma C L Marrs, John D Perry, J Jonathan Harburn

Index: Org. Lett. 14(24) , 6310-3, (2012)

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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.

Related Compounds

  • Spermine
  • Rhodanine

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