Synthesis of (+)-amberketal and its analog from l-abietic acid

Tetrahedron

Volumn 63, Issue 39, 2007, Pages 9896-9902

  Yadav, J S ^a   Baishya, Gakul ^a   Dash, Uttam ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

, Epoxyketone cyclization; (+) Amberketal; l Abietic acid; Regioselective dihydroxylation

Indexed keywords

ABIETIC ACID; ACETAL DERIVATIVE; ALDEHYDE; IODIDE; KETONE; NICKEL; PERFUME;

AQUEOUS SOLUTION; ARTICLE; DERIVATIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 34547760767     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.063     Document Type: Article

References (30)

1. Ohloff G. The Fragrance of Ambergris. In: Theimer E.T. (Ed). Fragrance Chemistry (1982), Academic, New York, NY 535-573
2. Bajgrowicz J.A., and Broger C. In: Baser K.H.C. (Ed). Proceedings of the 13th International Congress of Flavours, Fragrances and Essential oil (1995), AREP Publications, Istanbul 1-15
3. Fráter G., Bajgrowicz J.A., and Kraft P. Tetrahedron 54 (1998) 7633-7703
4. Kraft P., Bajgrowicz J.A., Denis C., and Fráter G. Angew. Chem., Int. Ed. 39 (2000) 2980-3010
5. Castro J.M., Salido S., Altarejos J., Nogueras M., and Sanchez A. Tetrahedron 58 (2002) 5941-5949
6. Bolster M.G., Langel B.M.F., Jansen B.J.M., Morin C., and Groot A. Tetrahedron 57 (2001) 8369-8379
7. Barrero A.B., Altarejos J., Alvarez-Manzaneda E., Ramos J.M., and Salido S. Tetrahedron 49 (1993) 6251-6262
8. Zahra J., Chauvet F., Coste-Maniere I., Martres P., Perfetti P., and Waegell B. Bull. Soc. Chim. Fr. 134 (1997) 1001-1024
9. Fehr C., and Faris I. Angew. Chem., Int Ed. 45 (2006) 6904-6907
10. Schenk H.R., Gutmann H., Jeger O., and Ruzicka L. Helv. Chim. Acta 37 (1954) 543-546
11. Scheidedegger U., Schaffner K., Jegger O., Schenk H.R., Gutmann H., Jeger O., and Ruzicka L. Helv. Chim. Acta 45 (1962) 400-435
12. Demole E. Experimentia 20 (1964) 609-610
13. Coste-Manière I.C., Zahra J.P., and Waegell B. Tetrahedron Lett. 29 (1988) 1017-1020
14. Martres P., Perfetti P., Zahra J.P., and Waegell B. Tetrahedron Lett. 32 (1991) 765-766
15. Martres P., Perfetti P., Zahra J.P., and Waegell B. Tetrahedron Lett. 35 (1994) 97-98
16. Martres P., Perfetti P., Zahra J.P., Waegell B., Giraudi E., and Petrzilka M. Tetrahedron Lett. 34 (1993) 8081-8084
17. Barrero A.F., Altarejos J., Alvarez-Manzaneda E.J., Ramos J.M., and Salido S. Tetrahedron 49 (1993) 9525-9534
18. Costa M.D.C., Tavares R., Motherwell W.B., and Curto M.J.M. Tetrahedron Lett. 35 (1994) 8839-8842
19. Buchbauer G., Heneis V.M., Krejci V., Talsky C., and Wunderer H. Monatsh. Chem. 116 (1985) 1345-1358
20. Koyama H., Kaku Y., and Ohno M. Tetrahedron Lett. 28 (1987) 2863-2867
21. Cambie R.C., Franich R.A., Larsen D., Rutledge P.S., Ryan G.R., and Woodgate P.D. Aust. J. Chem. 43 (1990) 21-46
22. Cambie R.C., Rutledge P.S., Ryan G.R., Strange G.A., and Woodgate P.D. Aust. J. Chem. 43 (1990) 867-881
23. Costa M.C., Alves S.P., Correia M.E., and Curto M.J.M. Synthesis (2006) 1171-1175
24. Garegg P.J., and Samuelson B. J. Chem. Soc., Perkin Trans. 1 (1980) 2866-2869
25. Garegg P.J., Johansson R., Ortega C., and Samuelson B. J. Chem. Soc., Perkin Trans. 1 (1982) 681-686
26. Chandrasekhar S., Narsihmulu Ch., Sultana S.S., and Reddy N.R. Chem. Commun. (2003) 1716-1717
27. Barrero A.F., Alvarez-Manzaneda E.J., Chahboun R., and Meneses R. Synlett (2000) 197-200
28. Barrero A.F., Alvarez-Manzaneda E.J., Chahboun R., and Meneses R. Synlett (1999) 1663-1666
29. Fieser L.F., and Fieser M. Reagents for Organic Synthesis Vol. 1 (1967), Wiley, New York, NY p 1179
30. Smith M.B. Oxidation. Organic Synthesis. 2nd ed. (2002), McGraw-Hill, New York, NY 258-263