Tetrahedron

Enantioselective synthesis of (S)-and (R)-fluoxetine hydrochloride

WH Miles, EJ Fialcowitz, ES Halstead

文献索引：Miles, William H; Fialcowitz, Elizabeth J; Scott Halstead Tetrahedron, 2001 , vol. 57, # 50 p. 9925 - 9929

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被引用次数: 44

摘要

The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2, 3-dihydrofuran (1) catalyzed by Ti [OCH (CH3) 2] 4/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine ...