Practical route to a new class of LTD4 receptor antagonists

Robert D. Larsen, Edward G. Corley, Anthony O. King, James D. Carroll, Paul Davis, Thomas R. Verhoeven, Paul J. Reider, Marc Labelle, Jacques Y. Gauthier, Yi Bin Xiang, Robert J. Zamboni

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Abstract

A general approach to the synthesis of a new class of LTD4 antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

Original languageEnglish (US)
Pages (from-to)3398-3405
Number of pages8
JournalJournal of Organic Chemistry
Volume61
Issue number10
DOIs
StatePublished - May 17 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Larsen, R. D., Corley, E. G., King, A. O., Carroll, J. D., Davis, P., Verhoeven, T. R., Reider, P. J., Labelle, M., Gauthier, J. Y., Xiang, Y. B., & Zamboni, R. J. (1996). Practical route to a new class of LTD4 receptor antagonists. Journal of Organic Chemistry, 61(10), 3398-3405. https://doi.org/10.1021/jo952103j