Selective formation of 4-ethoxy-5-methylene-2-cyclopentenones and 3-ethoxy-2-(1'-morpholinoalkenyl)-2-cyclopentenones from (1-ethoxy-3-morpholino-alkenylidene)pentacarbonylchromium complexes and terminal alkynes - A short enantioselective synthesis of the hypotensive oudenone

Bernard L. Flynn, Claudio C. Silveira, Armin De Meijere

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22 Citations (Scopus)

Abstract

(1-Ethoxy-3-morpholino-alkenylidene)pentacarbonylchromium complexes 1a-c react with terminal alkynes in DME to selectively give 4-ethoxy-5-(1'-morpholinoalkylidene)-2-cyclopentenones 3a,I and 3b,II and in THF/acetonitrile (9:1) to give 2-(1'-morpholinoalkenyl)-3-ethoxy-2-cyclopentenones 4a-c,I-IV in good to excellent yields (62-97%). Product 11b, an appropriately substituted derivative of 4, has been utilized in a short enantioselective synthesis of the tyrosine hydroxylase inhibiting natural product oudenone (13) from 1-pentynal (8).

Original languageEnglish
Pages (from-to)812-814
Number of pages3
JournalSynlett
Volume1995
Issue number8
DOIs
Publication statusPublished - 1 Aug 1995
Externally publishedYes

Keywords

  • cyclopentenones, functionally substituted
  • Fischer carbene complexes
  • oudenone
  • total synthesis
  • α,β-unsaturated

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