Title

Studies on the Enantioselective Synthesis of Cymbalta?

Authors

Kenneth Feldman

Document Type

Article

Publication Date

2009

Abstract

The enantioselective synthesis of Cymbalta? is reported. Cymbalta? is a serotonin reuptake inhibitor intended for individuals with major depressive disorder (MDD), generalized anxiety disorder (GAD), and pain related to diabetic neuropathy. Cymbalta? is unique because it can provide protection from especially severe symptoms where other drugs cannot ( for instance Prozac?). Consequently, Cymbalta? is an excellent synthetic target. Our synthetic route of Cymbalta? first establishes asymmetry by use of oxynitrilase, an enzyme isolated from raw almonds which is used to establish a chiral center in crotonaldehyde to yield (R)-cyanohydrin. This (R) asymmetry is maintained while adding functional groups to the molecular backbone. Reactions with academic importance are the addition of thiophene via Grubbs metathesis and alpha-naphthol via palladium catalysis. The three reactions mentioned above have successfully yielded the desired product, which proves our synthetic route to be a strong candidate for the enantioselective production of Cymbalta.

Advisor

Don Deardorff

Department

chem

Support

Howard Hughes Medical Institute Undergraduate Science Education Grant



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