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Synfacts 2010(10): 1104-1104  
DOI: 10.1055/s-0030-1258075
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Triple Reuptake Inhibitor (-)-GSK1360707

Contributor(s): Philip Kocienski
V. I. Elitzin, K. A. Harvey, H. Kim, M. Salmons, M. J. Sharp*, E. A. Tabet, M. A. Toczko
GlaxoSmithKline, Durham, USA
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

(-)-GSK1360707 is a serotonin-­noradrenaline-dopamine triple reuptake inhibitor under development for the treatment of severe depression. A five-step synthesis (21% overall yield) that afforded 10 kg of (-)-GSK1360707 features a double alkylative cyclopropanation of the lithium enolate derived from D using chloroiodomethane as the electrophile. The enantiomers of G were separated by chromatography on 20 x 25 cm ChiralPak columns with a throughput of 7.2 kg/day.