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Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines

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Sunderland Pharmacy School, Department of Pharmacy, Health & Well Being, University of Sunderland, Wharncliffe Street, Sunderland, SR1 3SD, U.K., Department of Biological Sciences, Institute of Structural and Molecular Biology, Birkbeck, University of London, Malet Street, Bloomsbury London, WC1E 7HX, U.K., Centre for Clinical Microbiology, Department of Infection, Royal Free Campus, University College London, London, NW3 2PF, U.K., Faculty of Pharmacy, The University of Sydney, Sydney, NSW 2006, Australia, Microbiological Department, Freeman Hospital, Newcastle-upon-Tyne, NE7 7DN, U.K., and School of Medicine, Pharmacy and Health, Wolfson Research Institute for Health and Wellbeing, Durham University, TS17 6BH, U.K.
†University of Sunderland.
‡University of London.
§University College London.
⊥The University of Sydney.
∥Freeman Hospital.
∇Durham University.
Cite this: Org. Lett. 2012, 14, 24, 6310–6313
Publication Date (Web):December 12, 2012
https://doi.org/10.1021/ol303057a
Copyright © 2012 American Chemical Society

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    Abstract

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    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.

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    Synthetic procedures, analytical and biological data for compounds 2ae, 3ae, 520. This material is available free of charge via the Internet at http://pubs.acs.org.

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