Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone

Tetrahedron

Volumn 61, Issue 46, 2005, Pages 10853-10860

  Blay, Gonzalo ^a   Collado, Ana M ^a   García, Begoña ^a   Pedro, José R ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Carbocation; Epoxides; Silicon; Spiroaxane sesquiterpenes; Wagner Merweein rearrangement

Indexed keywords

AXENOL; CARVONE; DECALIN; GLEENOL; SESQUITERPENE; SILICON; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; ROBINSON ANNULATION;

EID: 26844460191     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.025     Document Type: Article

References (43)

1. P.M. Dewick Nat. Prod. Rep. 19 2002 181 222 and previous reviews in this series
2. J.A. Marshall, S.F. Brady, and N.H. Andersen Fortschr. Chem. Org. Naturst. 31 1974 283 285
3. R. Robinson The Structural Relations of Natural Products 1955 Clarendon Oxford p 12
4. M.D. Eggers, V. Sinnwell, and E. Stahl-Biskup Phytochemistry 51 1999 987 990
5. V. Bargues, G. Blay, L. Cardona, B. García, and J.R. Pedro Tetrahedron 54 1998 1845 1852
6. V. Bargues, G. Blay, L. Cardona, A. Collado, B. García, M.C. Muñoz, and J.R. Pedro J. Org. Chem. 65 2000 2138 2144
7. G. Blay, L. Cardona, B. García, L. Lahoz, and J.R. Pedro Eur. J. Org. Chem. 2000 2145 2151
8. G. Blay, L. Cardona, B. García, L. Lahoz, B. Monje, and J.R. Pedro Tetrahedron 56 2000 6331 6338
9. G. Blay, V. Bargues, L. Cardona, B. García, and J.R. Pedro J. Org. Chem. 65 2000 6703 6707
10. G. Blay, L. Cardona, B. García, L. Lahoz, and J.R. Pedro J. Org. Chem. 66 2001 7700 7705
11. G. Blay, V. Bargues, L. Cardona, B. García, and J.R. Pedro Tetrahedron 57 2001 9719 9725
12. R.M. Coates Fortschr. Chem. Org. Naturst. 33 1976 73 230
13. D. Caine, and S.L. Graham J. Org. Chem. 45 1980 3790 3797
14. N.H. Andersen, M.S. Falcone, and D.D. Syrdal Tetrahedron Lett. 21 1970 1759 1762
15. P. Ceccherelli, M. Curini, M.C. Marcotullio, and O. Rosati Tetrahedron 45 1989 3809 3818
16. I. Kitagawa, Y. Yamazoe, R. Takeda, and I. Yosioka Tetrahderon Lett. 48 1972 4843 4846
17. J.M. Coxon, and N.B. Lindley Aust. J. Chem. 29 1976 2207 2217
18. H. Hikino, T. Kohama, and T. Takemoto Tetrahedron 25 1969 1037 1045
19. G. Mehta, G.L. Chetty, U.R. Nayak, and S. Dev Tetrahedron 24 1968 3775 3786
20. G. Blay, L. Cardona, A.M. Collado, B. García, and J.R. Pedro Tetrahedron Lett. 44 2003 8117 8119
21. G. Blay, A.M. Collado, B. García, V. Morcillo, and J.R. Pedro J. Org. Chem. 69 2004 7294 7302
22. J.R. Hwu, and J.M. Wetzel J. Org. Chem. 57 1992 922 928
23. E.W. Colvin Silicon Reagents in Organic Synthesis 1988 Academic London
24. P.I. Kurvyakov, Y.V. Gatilov, V. Yu, V.A. Khan, Zh.V. Dubovenko, and V.A. Pentegova Khim. Prir. Soedin. 1979 164 168
25. V.A. Khan, Zh.V. Dubovenko, and V.A. Pentegova Khim. Prir. Soedin. 1983 109 110
26. S. Nagahama, M. Tazaki, H. Nomura, K. Nishimura, M. Tajima, and Y. Iwasita Mokuzai Gakkaishi 42 1996 1127 1133
27. A.F. Barrero, J.F. Sánchez, J.E. Oltra, J. Altarejos, N. Ferrol, and A. Barragan Phytochemistry 30 1991 1551 1554
28. S. de Rosa, A. de Giulio, C. Iodice, and N. Zavodink Phytochemistry 37 1994 1327 1330
29. C.J. Barrow, J.W. Blunt, and M.H.G. Munro Aust. J. Chem. 41 1988 1755 1761
30. B. Bozan, T. Ozek, M. Kurkcuoglu, N. Kirimer, K. Baser, and C. Husnu Planta Med. 65 1999 781 782
31. D. Caine, and H. Deutsch J. Am. Chem. Soc. 100 1978 8030 8031
32. S. Ohira, N. Yoshihara, and T. Hasegawa Chem. Lett. 1998 739 740
33. K. Oesterreich, and D. Spitzner Tetrahedron 58 2002 4331 4334
34. K. Oesterreich, I. Klein, and D. Spitzner Synlett 2002 1712 1714
35. W.C. Still J. Org. Chem. 41 1976 3063 3064
36. A.V. Baranovsky, B.J.M. Jansen, T.M. Meulemans, and A. de Groot Tetrahedron 54 1998 5623 5634
37. B.J.M. Jansen, J.A. Kreuger, and A. de Groot Tetrahedron 45 1989 1447 1452
38. A.A. Verstegen-Haaksma, H.J. Swarts, B.J.M. Jansen, and A. de Groot Tetrahedron 50 1994 10073 10082
39. V.N. Zhabinskii, A.J. Minnaard, J.B.P.A. Wijnberg, and A. de Groot J. Org. Chem. 61 1996 4022 4027
40. R. Krieg, and B. Schönecker Liebigs Ann. Chem. 1994 1025 1032
41. T. Imamoto, N. Takiyama, N. Nakamura, T. Hatajima, and Y. Kamiya J. Am. Chem. Soc. 111 1989 4392 4398
42. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 3rd ed. 1988 Pergamon Oxford
43. 13C NMR δ 215.3 (s), 211.4 (s), 207.3 (s), 146.8 (s), 110.5 (t), 50.6 (s), 47.1 (d), 43.6 (d), 42.3 (t), 40.0 (t), 39.3 (t), 33.2 (d), 29.8 (q), 29.2 (q), 27.3 (t), 26.8 (t), 21.8 (q), 20.8 (q), 0.2 (q).