Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

doi:10.1016/S0040-4020(99)00456-1

Tetrahedron

Volume 55, Issue 29, 16 July 1999, Pages 8967-8976

https://doi.org/10.1016/S0040-4020(99)00456-1 Get rights and content

Abstract

Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described.

A rapid synthesis of the SSRI sertraline is described starting from a dihydronaphthalenol, readily available via catalytic asymmetric reductive ring opening of oxabenzonorbornadiene.

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Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

Abstract

Tetrahedron Lett.

Tetrahedron Lett.

Tetrahedron

Chem. Ind. (London)

Tetrahedron Lett.

Tetrahedron Lett.

Tetrahedron Lett.

Analytical Profiles of Drug Substances and Excipients

Chem. Rev.

J. Med. Chem.

J. Med. Chem.

J. Med. Chem.

J. Med. Chem.

J. Med. Chem.

J. Med. Chem.

Tetrahedron

J. Org. Chem.

J. Org. Chem.

J. Med. Chem.

J. Am. Chem. Soc.

J. Org. Chem.