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Synlett 1996; 1996(11): 1087-1090
DOI: 10.1055/s-1996-5689
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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
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Publication Date:
31 December 2000 (online)

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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