Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (±)-α- and β-cedrene by preparation of cedrone

Tetrahedron

Volumn 62, Issue 49, 2006, Pages 11360-11370

  Crawford, James J ^a   Kerr, William J ^a   McLaughlin, Mark ^a   Morrison, Angus J ^a   Pauson, Peter L ^a   Thurston, Graeme J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Cedrene; Cobalt; Pauson Khand reaction; Stereoselective Wittig reaction; Tricyclic sesquiterpene

Indexed keywords

ALKENE; ALPHA CEDRENE; CEDRENE; CEDRONE; KETONE; SESQUITERPENE DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PAUSON KHAND REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 33750432868     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.044     Document Type: Article

References (56)

1. Barrero A.F., del Moral J.Q., and Lara A. Tetrahedron 56 (2000) 3717 and references therein
2. Stork G., and Breslow R. J. Am. Chem. Soc. 75 (1953) 3291
3. Walter P. Ann. Chem. 39 (1841) 247
4. For example, see:
5. Stork G., and Clark Jr. F.H. J. Am. Chem. Soc. 77 (1955) 1072
6. Corey E.J., Girotra N.N., and Mathew C.T. J. Am. Chem. Soc. 91 (1969) 1557
7. Crandall T.G., and Lawton R.G. J. Am. Chem. Soc. 91 (1969) 2127
8. Kuehne M.E., and Damon R.E. J. Org. Chem. 42 (1977) 1825
9. Breitholle E.G., and Fallis A.G. J. Org. Chem. 43 (1978) 1964
10. Wender P.A., and Howbert J.J. J. Am. Chem. Soc. 103 (1981) 688
11. Rigby J.H., and Kirova-Snover M. Tetrahedron Lett. 38 (1997) 8153
12. Lee H.-Y., Lee S., Kim D., Kim B.K., Bahn J.S., and Kim S. Tetrahedron Lett. 39 (1998) 7713
13. Caldwell J.J., Cameron I.D., Christie S.D.R., Hay A.M., Johnstone C., Kerr W.J., and Murray A. Synthesis (2005) 3293
14. Brown J.A., Janecki T., and Kerr W.J. Synlett (2005) 2023
15. Brown J.A., Irvine S., Kerr W.J., and Pearson C.M. Org. Biomol. Chem. 3 (2005) 2396
16. Kerr W.J., McLaughlin M., and Pauson P.L. J. Organomet. Chem. 630 (2001) 118
17. Kerr W.J., McLaughlin M., Pauson P.L., and Robertson S.M. J. Organomet. Chem. 630 (2001) 104
18. Kennedy A.R., Kerr W.J., Lindsay D.M., Scott J.S., and Watson S.P. J. Chem. Soc., Perkin Trans. 1 (2000) 4366
19. Brown D.S., Campbell E., Kerr W.J., Lindsay D.M., Morrison A.J., Pike K.G., and Watson S.P. Synlett (2000) 1573
20. Ford J.G., Kerr W.J., Kirk G.G., Lindsay D.M., and Middlemiss D. Synlett (2000) 1415
21. Kerr W.J., Lindsay D.M., McLaughlin M., and Pauson P.L. Chem. Commun. (2000) 1467
22. Carbery D.R., Kerr W.J., Lindsay D.M., Scott J.S., and Watson S.P. Tetrahedron Lett. 41 (2000) 3235
23. Kerr W.J., Lindsay D.M., Rankin E.M., Scott J.S., and Watson S.P. Tetrahedron Lett. 41 (2000) 3229
24. Kerr W.J., Lindsay D.M., and Watson S.P. Chem. Commun. (1999) 2551
25. Kerr W.J., McLaughlin M., Pauson P.L., and Robertson S.M. Chem. Commun. (1999) 2171
26. Clements C.J., Dumoulin D., Hamilton D.R., Hudecek M., Kerr W.J., Kiefer M., Moran P.H., and Pauson P.L. J. Chem. Res. (S) 636 (1998) (M) 2658
27. Donkervoort J.G., Gordon A.R., Johnstone C., Kerr W.J., and Lange U. Tetrahedron 52 (1996) 7391
28. Kerr W.J., Kirk G.G., and Middlemiss D. Synlett (1995) 1085
29. Gordon A.R., Johnstone C., and Kerr W.J. Synlett (1995) 1083
30. Hay A.M., Kerr W.J., Kirk G.G., and Middlemiss D. Organometallics 14 (1995) 4986
31. Johnstone C., Kerr W.J., and Lange U. J. Chem. Soc., Chem. Commun. (1995) 457
32. Kerr W.J., McLaughlin M., Morrison A.J., and Pauson P.L. Org. Lett. 3 (2001) 2945
33. Ito Y., Hirao T., and Saegusa T. J. Org. Chem. 43 (1978) 1011
34. Tsuji J., Minami I., and Shimizu I. Tetrahedron Lett. 24 (1983) 5635
35. Minami I., Takahashi K., Shimizu I., Kimura T., and Tsuji J. Tetrahedron 42 (1986) 2971
36. Kobayashi S., Hachiya I., Takahori T., Araki M., and Ishitani H. Tetrahedron Lett. 33 (1992) 6815
37. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
38. Ohira S. Synth. Commun. 19 (1989) 561
39. Müller S., Liepold B., Roth G.J., and Bestmann H.J. Synlett (1996) 521
40. Shambayati S., Crowe W.E., and Schreiber S.L. Tetrahedron Lett. 31 (1990) 5289
41. Jeong N., Chung Y.K., Lee B.Y., Lee S.H., and Yoo S.-E. Synlett (1991) 204
42. Chung Y.K., Lee B.Y., Jeong N., Hudecek M., and Pauson P.L. Organometallics 12 (1993) 220
43. Krafft M.E., Scott I.L., Romero R.H., Feibelmann S., and Van Pelt C.E. J. Am. Chem. Soc. 115 (1993) 7199
44. Sugihara T., Yamada M., Yamaguchi M., and Nishizawa M. Synlett (1999) 771
45. Kennedy A.R., Kerr W.J., McLaughlin M., and Pauson P.L. Acta Crystallogr. C57 (2001) 1316
46. Kelly S.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon, Oxford 729
47. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863
48. Vedejs E., Meier G.P., and Snoble K.A.J. J. Am. Chem. Soc. 103 (1981) 2823
49. Vedejs E., Marth C.F., and Ruggeri R. J. Am. Chem. Soc. 110 (1988) 3940
50. Vedejs E., and Marth C.F. J. Am. Chem. Soc. 110 (1988) 3948
51. Schlosser M., Schaub B., de Oliveira-Neto J., and Jeganathan S. Chimia 40 (1986) 244
52. Schlosser M., and Schaub B. J. Am. Chem. Soc. 104 (1982) 5821
53. Barton D.H.R., and McCombie S.W. J. Chem. Soc., Perkin Trans. 1 (1975) 1574
54. Hartwig W. Tetrahedron 39 (1983) 2609
55. Johnstone C., Kerr W.J., and Scott J.S. J. Chem. Soc., Chem. Commun. (1996) 341
56. Caldwell, J. J.; Kerr, W. J.; Scott, J. S.; Shearer, G. C. Unpublished results.