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Synlett 1991; 1991(5): 337-338
DOI: 10.1055/s-1991-34729
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Chiral, Nonracemic Bridgehead Amine: Bridgehead Olefin of a New Tricyclic Sesquiterpene

H. Martin R. Hoffmann* , Ulrike Eggert
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-3000 Hannover, Germany
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Publication Date:
07 March 2002 (online)

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(1S,2S,5R)-1-Amino-4,4-dimethyltricyclo[6.3.2.02,5]tridec-8(9)-ene (5) was prepared from (-)-caryophyllene oxide (1) in six steps. The key carbon-nitrogen bond was formed by treatment of the corresponding bridgehead acetate with trimethylsilyl azide in the presence of aluminum chloride.