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

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

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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