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Synthesis 2006(7): 1171-1175  
DOI: 10.1055/s-2006-926392
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of an Ambergris-Type Ketal from Abietic Acid

M. Céu Costa*, S. P. Alves, M. Eduarda Correia, M. João Marcelo-Curto
Instituto Nacional de Engenharia Tecnologia e Inovação, Estrada do Paço do Lumiar, Ed. F, 1649-038 Lisbon, Portugal
Fax: +351(21)7168100; e-Mail: ceu.costa@mail2.ineti.pt;
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Publication History

Received 21 October 2005
Publication Date:
14 March 2006 (online)

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Abstract

Abietic acid, the main component of pine rosin, was used as starting material for the hemisynthesis of the ambergris-type ketal. The key intermediate step consisted of the synthesis of an exocyclic olefin through appropriate handling of a very sensitive aldehyde generated as an intermediate precursor.

Key words

ambergris perfume - rosin - abietic acid - ketalization

    References

  • 1a Ohloff G. The Fragrance of Ambergris, In Fragrance Chemistry   Theimer ET. Academic Press; New York: 1982.  p.535-573  
  • 1b Bajgrowicz JA. Broger C. In Procedures of the 13th International Congress of Flavours, Fragrances and Essential Oils   Baser KHC. AREP Publications; Istanbul: 1995.  p.1-15  
  • 1c Dimoglo AS. Vlad PF. Shvets NM. Coltsa MN. Güzel Y. Saraçoglu M. Saripinar E. Patat S. New J. Chem.  1995,  19:  1217 
  • 1d Gorbachov MY. Rossiter K. J. Chem. Senses  1999,  24:  171 
  • 1e Kraft P. Bajgrowicz JA. Denis C. Fráter G. Angew. Chem. Int. Ed.  2000,  39:  2980 
  • 2a Castro JM. Salido S. Altarejos J. Nogueras M. Sánchez A. Tetrahedron  2002,  58:  5941 
  • 2b Bolster MG. Lagnel BMF. Jansen BJM. Morin C. Groot A. Tetrahedron  2001,  57:  8369 
  • 2c Barrero AB. Altarejos J. Alvarez-Manzaneda E. Ramos JM. Salido S. Tetrahedron  1993,  49:  9525 
  • 2d Barrero AB. Alvarez-Manzaneda E. Altarejos J. Salido S. Ramos JM. Tetrahedron  1993,  49:  10405 
  • 2e Zahra J. Chauvet F. Coste-Maniére I. Martres P. Perfetti P. Waegell B. Bull Soc. Chim. Fr.  1997,  134:  1001 
  • 2f Nishi Y. Ishihara H. Jpn. Oil Chem. Soc.  1989,  38:  276 
  • 2g Nunes FMN. Imamura PM. J. Braz. Chem. Soc.  1996,  7:  181 
  • 3 Fráter G. Bajgrowicz JA. Kraft P. Tetrahedron  1998,  54:  7633 
  • 4 Martres P. Perfetti P. Zahra J.-P. Waegell B. Giraudi E. Petrzilka M. Tetrahedron Lett.  1993,  34:  8081 
  • 5a Costa MC. Ph.D. Thesis   Faculty of Pharmacy, University of Lisbon; Portugal: 1992. 
  • 5b Costa MC. Tavares R. Motherwell WB. Marcelo Curto MJ. Tetrahedron Lett.  1994,  35:  8839 
  • 6 Cambie RC. Franich RA. Larsen D. Rutledge PS. Ryan GR. Woodgate PD. Aust. J. Chem.  1990,  43:  21 
  • 7 Cambie RC. Rutledge PS. Ryan GR. Strange GA. Woodgate PD. Aust. J. Chem.  1990,  43:  867 
  • 8 Buchbauer G. Heneis VM. Krejci V. Talsky C. Wunderer H. Monatsh. Chem.  1985,  116:  1345 
  • 9 Koyama H. Kaku Y. Ohno M. Tetrahedron Lett.  1987,  28:  2863 
  • 10 Winter B. Pure Appl. Chem.  1990,  62:  1377 
  • 11 Santos C. Zukerman-Schpector J. Imamura PM. J. Braz. Chem. Soc.  2003,  14:  998 
  • 12 Barrero AF. Alvarez-Manzaneda EJ. Chahboun R. Meneses R. Synlett  2000,  197 
  • 13 Barrero AF. Alvarez-Manzaneda EJ. Chahboun R. Meneses R. Synlett  1999,  1663 
  • 14 Garegg PJ. Samuelsson B. J. Chem. Soc., Perkin Trans. 1  1980,  2866 
  • 15 Garegg PJ. Johansson R. Ortega C. Samuelsson B. J. Chem. Soc., Perkin Trans. 1  1982,  681 
  • 16 Aoyagi S. Hirashima S. Saito K. Kibayashi C. J. Org. Chem.  2002,  67:  5517 
  • 17 Phukan P. Bauer M. Maier M. Synthesis  2003,  1324