Synthesis of ‘Spacer’-Naproxen [2-(6-Methoxybiphenylen-2-yl)propanoic Acid] and -Isonaproxen [2-(7-Methoxybiphenylen-2-yl)propanoic Acid]

Authors

Juan A. González Gómez
James R. Green, University of WindsorFollow
Peter C. Vollhardt, University of California - BerkeleyFollow

Document Type

Article

Publication Date

4-2011

Publication Title

Synlett

Volume

2011

Issue

6

First Page

805

Keywords

alkynes, cobalt, cyclization, carbocycles, regioselectivity

Last Page

808

Abstract

The CpCo(CO)₂-catalyzed cocyclization of 1,2-diethynyl- 4-methoxybenzene with alkynes can be applied to the synthesis of ‘spacer’-naproxen [2-(6-methoxybiphenylen-2-yl)propanoic acid] and its 7-methoxy isomer, ‘spacer’-isonaproxen. While unsymmetrical alkynes are incorporated without regioselectivity, the methoxy group in 6-methoxy-2,3-bis(trimethylsilyl)biphenylene directs electrophiles to C-3, thus allowing for regiochemical differentiation between the 2- and 3-positions.

DOI

10.1055/s-0030-1259718

Funding Reference Number

NSF (CHE-0907800)

Comments

First published in Synlett, copyright © Georg Thieme Verlag, an imprint of Thieme Publishing. To access the final version, see DOI: 10.1055/s-0030-1259718 at https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0030-1259718.

Recommended Citation

González Gómez, Juan A.; Green, James R.; and Vollhardt, Peter C.. (2011). Synthesis of ‘Spacer’-Naproxen [2-(6-Methoxybiphenylen-2-yl)propanoic Acid] and -Isonaproxen [2-(7-Methoxybiphenylen-2-yl)propanoic Acid]. Synlett, 2011 (6), 805-808.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/72