Download PDF
Synlett 1995; 1995(8): 812-814
DOI: 10.1055/s-1995-5085
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

(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