Chemo-enzymatic synthesis of the antidepressant duloxetine and its enantiomer.
Sodium borohydride reduction of 3-chloro-1-(2-thienyl)-1-propanone gave the corresponding racemic alcohol which was kinetically resolved with lipase B from Candida antarctica as catalyst to yield the chiral building blocks (S)-3-chloro-1-(2-thienyl)-1-propanol and the corresponding (R)-butanoate. The enantiopure chiral building blocks were converted into Duloxetine and its enantiomer.
Liu
H
H
Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway.
Hoff
B H
BH
Anthonsen
T
T
D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000302:isolation & purification; D002175:Candida / Q000201:enzymology; D000068736:Duloxetine Hydrochloride; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000302:isolation & purification
D000928:Antidepressive Agents; D013876:Thiophenes; D000068736:Duloxetine Hydrochloride; D008049:Lipase