Download PDF
Synlett 1996; 1996(11): 1087-1090
DOI: 10.1055/s-1996-5689
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.

Trifunctional Reagents in Organic Synthesis: Sequential, Chemoselective Reactions Leading to the Preparation of Structurally Novel Tricycles

Edward Piers* , Ernest J. McEachern
  • *Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1, Fax 1(604)8222847, Bitnet epier@unixg.ubc.ca
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The synthetic utility of the structurally novel trifunctional reagents 11-13 is described. Using 11-13 and the 3-isobutoxycyclohex-2-en-1-ones 14 and 28 as starting materials, the enones 18-20 and 31-33 are readily prepared. Copper(I) cyanide-mediated intramolecular conjugate addition of each of these enones provides good-to-excellent yields of the corresponding bicyclo[4.3.0]non-8-en-3-ones 21-23 and 34-36. Intramolecular alkylation of the latter substances affords the structurally novel tricyclic ketones 24-26 and 37-39, respectively, in high yields.

copper(I) cyanide-mediated intramolecular conjugate addition - copper-tin transmetallation - intramolecular alkylation - vinylcopper(I) species - organostannane compounds

      >