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Synlett 1995; 1995(8): 812-814
DOI: 10.1055/s-1995-5085
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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*
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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(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).

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