Synthesis of an ambergris-type ketal from abietic acid

Synthesis

Volumn , Issue 7, 2006, Pages 1171-1175

  Costa, M Céu ^a   Alves, S P ^a   Correia, M Eduarda ^a   Marcelo Curto, M João ^a  

^a INETI   (Portugal)

Author keywords

Abietic acid; Ambergris perfume; Ketalization; Rosin

Indexed keywords

ALDEHYDES; AMINO ACIDS; OLEFINS; SYNTHESIS (CHEMICAL);

ABIETIC ACID; AMBERGRIS PERFUME; KETALIZATION; ROSIN;

KETONES;

ABIETIC ACID; ACETAL; ALDEHYDE; ALKENE; AMBERGRIS; PERFUME; ROSIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; INFRARED SPECTROSCOPY; NONHUMAN; ODOR; PINE; PORTUGAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33645980372     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926392     Document Type: Article

References (28)

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