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Synfacts 2010(9): 0977-0977  
DOI: 10.1055/s-0030-1257879
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Paroxetine

Contributor(s): Philip Kocienski
M.-h. Kim, Y. Park, B.-S. Jeong, H.-g. Park*, S.-s. Jew*
Seoul National University and Yeungnam University, Gyeongsan, Korea
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

(-)-Paroxetine is a selective serotonin reuptake inhibitor that is used to treat anxiety, depression, and panic disorders. The synthesis depicted (15 steps, 9.1% overall yield) features an asymmetric phase-transfer-catalyzed alkylation of the N,N-bis(4-methoxyphenyl)malonamide tert-butyl ester B. The reaction required only 1 mol% of the Maruoka catalyst A. The scale of the reaction is not given.