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Original Articles

Synthesis of (-)-8-Epiambreinolide. Formal Synthesis of Ambraoxide

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Pages 183-186 | Received 23 Aug 1994, Published online: 04 Oct 2006

References

  • Ohloff , G. 1982 . “ The Fragrance of Ambergris ” . In Fragrance Chemistry. The Science of the Sense and Smell , Edited by: Theimer , T. H. 535 – 573 . New York : Academic Press .
  • Jegou , E. , Polonsky , J. , Lederer , E. , Schulte-Elte , K. H. , Egger , B. and Ohloff , G. 1977 . Ambergris revisited. Isolation of volatile constituents; identification and synthesis of Ambra-Aldehyde C14H22 O . Nouveau Journal de Chimie , 1 : 529 – 531 .
  • Büchi , G. and Wüest , H. 1989 . The Synthesis of Racemic Ambrox® . Helvetica Chimica Acta , 72 : 996 – 1000 . Cyclization of (+) 3 with p-toluensulfonic acid in nitromethane gave the kinetically controlled diasteroisomer 4 (racemic). See
  • Ohloff , G. , Vial , C. , Wolf , H. R. , Job , K. , Jegou , E. , Polonsky , J. and Lederer , E. 1980 . Stereochemistry-Odor Relationship in Enantiomeric Ambergris Fragrances . Helvetica Chimica Acta , 63 : 1932 – 1946 .
  • Dominguez , G. , Marco , J. L. , Hueso-Rodriguez , J. A. and Rodriguez , B. 1988 . Transformaciones de Hipanolona. VI. Hemisintesis de (+)Ambreinolida y (-)-8-Epiambreinolida . Anales de Químia (España) , 84 : 211 – 214 .
  • Appel , H. H. , Brooks , C. J.W. and Overton , K. H. 1959 . The Constitution and Stereochemistry of Drimenol, A Novel Bicyclic Sesquiterpenoid . Journal of the Chemical Society , : 3322 – 3332 .
  • Hlubucek , J. R. , Aasen , A. J. , Almqvist , S. and Enzell , C. R. 1974 . Tobacco Chemistry. 25. Two New Drimane Sesquiterpene. Alcohols from Greek Nicotiana tabacum, L . Acta Chemica Scandinavica , 28 : 289 – 294 .
  • Satisfactory elemental analysis and spectral data were obtained for all new compounds. Selected physical properties and spectral data. 2: m.p. 109–110°C (hexane) lit5 108–110°C. [α]D 20 - 28.5(c, 1; CHCl3) lit5–31.5°(c, 0.089, CHCl3), ir (KBr) 2935, 1730, 1245, 1025 cm−1. 1H nmr (100 MHz, CDCl3, δ ppm) 0.7(s, 3H), 0.82(s, 6H, 2×CH3), 1.27(s, 3H), 2.6(m, 2H). 3: m.p. 145–147°C (CHCl3); [α]D 20 + 18°(c, 1; CHCl3) ir (KBr) 3400–3200, 2940, 1100; 1H mnr 0.82(s, 3H), 0.86(s, 3H), 0.95(s, 3H, CH3), 1.1(s, 3H), 3.70(m, 2H)

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