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Synthesis 2000; 2000(9): 1247-1252
DOI: 10.1055/s-2000-6415
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Homoallylic Assistance on the Reduction of endo-2,5-Dibromotricyclone-[6.2.1.02,7]undeca-4,9-diene-3,6-dione through NaBH4/CeCl3 · 6 H2O: Synthesis and Characterization of 5-Bromo-12-oxa-pentacyclo[6.2.1.16,9.02,7.02,10]dodeca-4-en-3-endo-ol

Fernando D. P. Morisso* , Katia Wagner, Manfredo Hörner, Robert Alan Burrow, Adailton J. Bortoluzzi, Valentim E. U. Costa
  • *Instituto de Química de Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves 9500, Porto Alegre, RS, Brazil; E-mail: valentim@if.ufrgs.br
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Publication Date:
31 December 2000 (online)

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The behavior of the tricyclic compounds 3, 4, and 5 towards reductive systems is described. The [4 + 2] cycloadduct 3, when reduced by NaBH4/CeCl3 · 6 H2O led to the isolation of the nortricyclenic compound 8 whereas the cycloadduct 4 provided the analog 9. The reduction of norbornenequinone 5 gave the aromatized compound 10 when performed by sodium dithionite or by NaBH4/CeCl3 · 6 H2O. The structure and stereochemistry of the hydroxyl group in the compound 8 was determined by NMR and confirmed by X-ray analysis. Also, some mechanistic considerations concerning the formation of the compounds 8 and 9 are presented.

bromine - Diels-Alder reactions - polycycles - reductions - ring closure

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