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Synfacts 2010(4): 0387-0387  
DOI: 10.1055/s-0029-1219490
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Sertraline

Contributor(s): Philip Kocienski
H. Ohmiya, Y. Makida, D. Li, M. Tanabe, M. Sawamura*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

A palladium-catalyzed regioselective and stereospecific allyl-aryl coupling between acyclic (E)-allylic esters and arylboronic acids (D → E) was the key step in a synthesis of the ­antidepressant (+)-sertraline. A study comprising more than 30 examples established that a broad range of functional groups is tolerated in both the allylic ester and the arylboronic acid. The allylic substitution also tolerates air and moisture.