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Synlett 2001; 2001(5): 0664-0666
DOI: 10.1055/s-2001-13373
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Base-Induced Rearrangement of Bicyclo[3.3.1]nonan-3-ones to Polysubstituted Hexahydronaphthalenes

Jon K. F. Geirsson* , Emelia G. Eiriksdottir
  • *Science Institute, University of Iceland, Dunhaga 3, IS-107 Reykjavik, Iceland; Fax + 354 552 8911; E-mail: jkfg@raunvis.hi.is
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Publikationsdatum:
31. Dezember 2001 (online)

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This Letter describes the stereoselective preparation of novel polysubstituted hexahydronaphthalene derivatives obtained when readily available bicyclo[3.3.1]nonan-3-ones were treated with DBU in acetone. A plausible pathway for this transformation is discussed and the aromatization on the products to form resorcinol derivatives is briefly noted.

hexahydronaphthalenes - bicyclo[3.3.1]nonan-3-ones - 1-tetralones - resorcinols