A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Debra J. Wallace, Jonathan M. Goodman, Derek J. Kennedy, Antony J. Davies, Cameron J. Cowden, Michael S. Ashwood, Ian F. Cottrell, Ulf H. Dolling, Paul J. Reider

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Abstract

Equation presented The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing matathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

Original languageEnglish (US)
Pages (from-to)671-674
Number of pages4
JournalOrganic Letters
Volume3
Issue number5
DOIs
StatePublished - Mar 8 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Wallace, D. J., Goodman, J. M., Kennedy, D. J., Davies, A. J., Cowden, C. J., Ashwood, M. S., Cottrell, I. F., Dolling, U. H., & Reider, P. J. (2001). A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists. Organic Letters, 3(5), 671-674. https://doi.org/10.1021/ol006958g