Synthesis of (±)-Campherenone, (±)-Epicampherenone, (±)-β-Santalene (±)-epi-β-Santalene, (±)α-Santalene, (±)Ylangocamphor, (±)- Copacamphor, and (±)-Sativene

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1973, Pages 2113-2130

  Hodgson, Gordon L ^a   Macsweeney, D F ^a   Money, Thomas ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORNANE DERIVATIVE; CAMPHOR; SESQUITERPENE;

ARTICLE; CHEMICAL MODEL; CYCLIZATION; SYNTHESIS; TECHNIQUE;

BORNANES; CAMPHOR; CYCLIZATION; METHODS; MODELS, CHEMICAL; SESQUITERPENES;

EID: 0015823901     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19730002113     Document Type: Article

References (67)

1. G. L. Hogdson, D. F. Mac- Sweeney, and T. Money, Chem. Comm., 1971, 766
2. G. L. Hogdson, D. F. Mac- Sweeney, and T. Money, Tetrahedron Letters, 1972, 3683.
3. J. C. Fairlie, G. L. Hodgson, and T. Money, preceding paper.
4. H. Hikino, N. Suzuki, and T. Takemoto, Chem. and Pharm. Bull. (Japan), 1971, 19, 87.
5. G. L. Hodgson, D. F. MacSweeney, R. W. Mills, and T. Money, J.C.S. Chem. Comm., 1973, 235.
6. V. Herout, V. Jarolim, and J. Pliva, Coll. Czech. Chem. Comm., 1957, 22, 773
7. E. J. Corey, R. Hartmann, and P. A. Vatakencherry, J. Amer. Chem. Soc., 1962, 84, 2611 and references cited therein.
8. E. Piers, R. W. Britton, R. J. Keziere, and R. D. Smillie, Canad. J. Chem., 1971, 49, 2620, 2623, and references cited therein.
9. E. Piers, M. B. Geraghty, F. Kido, and M. Soucy, Synth. Comm., 1972, 3, 39.
10. D. H. R. Barton and N. H. Werstiuk, J. Chem. Soc. (C), 1968, 148.
11. M. Kolbe-Haugwitz and L. Westfelt, Acta Chem. Scand., 1970, 24, 1623 and references cited therein.
12. P. de Mayo and R. E. Williams, J. Amer. Chem. Soc., 1965, 87, 3275.
13. S. Huneck and E. Klein, Phytochemistry, 1967, 6, 383.
14. F. Kido, R. Sakuma, H. Uda, and A. Yoshikoshi, Tetrahedron Letters, 1969, 3169
15. N. H. Anderson, Tetrahedron Letters, 1970, 1755, 4651.
16. L. A. Smedman, E. Zavarin, and R. Teranishi, Phytochemistry, 1969, 1457.
17. L. A. Smedman and E. Zavarin, Tetrahedron Letters, 1968, 3833
18. T. Norin, Phytochemistry, 1972, 11, 1231.
19. S. C. Bisarya and S. Dev, Tetrahedron Letters, 1964, 3751
20. S. Akiyoshi, H. Erdtmann, and T. Kubota, Tetrahedron, 1960, 9, 237.
21. G. Ourisson, Bull. Soc. chim. France, 1955, 22, 895
22. G. Ourisson, Proc. Chem. Soc., 1964, 274.
23. V. R. Nayak and S. Dev, Tetrahedron Letters, 1963, 243.
24. J. L. Simonsen and D. H. R. Barton, ‘The Terpenes,’ vol. Ill, Cambridge University Press, 1952.
25. H. C. Kretschmar and W. F. Erman, Tetrahedron Letters, 1970, 41.
26. E. J. Corey and H. Yamamoto, J. Amer. Chem. Soc., 1970, 92, 226
27. E. J. Corey, H. A. Kirst, and J. A. Katzenellenbogen, J. Amer. Chem. Soc., p. 6314
28. R. G. Lewis, D. H. Gustafson, and W. F. Erman, Tetrahedron Letters, 1967, 401.
29. H. C. Kretschmar, Z. S. Barneis, and W. F. Erman, Tetrahedron Letters, 1970, 37.
30. A. Homma, M. Kato, M. Wu, and A. Yoshikoshi, Tetrahedron Letters, 1970, 231
31. N. H. Anderson, Tetrahedron Letters, p. 1755.
32. F. Kido, R. Sakuma, H. Uda, and A. Yoshikoshi, Tetrahedron Letters, 1969, 3169.
33. K. Doi, T. Shibuya, T. Matsuo, and S. Miki, Tetrahedron Letters, 1971, 4003.
34. B. W. Roberts, M. S. Poonian, and S. C. Welch, J. Amer. Chem. Soc., 1969, 91, 3400.
35. P. de Mayo, R. Robinson, E. Y. Spencer, and R. W. White, Canad. J. Chem., 1963, 41, 2996
36. P. de Mayo, R. E. Williams, and E. Y. Spencer, Canad. J. Chem., 1965, 43, 1357.
37. K. W. Turnbull, W. Acklin, D. Arigoni, A. Corbella, P. Gariboldi, and G. Jommi, J.C.S. Chem. Comm., 1972, 598 and references cited therein.
38. W. Parker, J. S. Roberts, and R. Ramage, Quart. Rev., 1967, 21, 331.
39. J. L. Simonsen and L. N. Owen, ‘The Terpenes,’ vol. II, Cambridge University Press, 1949.
40. C. H. Heathcock, J. E. Ellis, and R. A. Badger, J. Heterocyclic Chem., 1969, 6, 139.
41. R. Crawford, W. F. Erman, and C. D. Broaddus, J. Amer. Chem. Soc., 1972, 94, 4298.
42. J. Trotter and S. J. Rettig, to be published.
43. J. Hooz and S. S. H. Gilani, Canad. J. Chem., 1968, 46, 86
44. I. M. Downie, J. B. Holmes, and J. B. Lee, Chem. and Ind., 1966, 900.
45. B. E. Edwards and P. N. Rao, J. Org. Chem., 1966, 31, 324.
46. J. D. Connolly and R. McCrindle, Chem. and Ind., 1965, 379
47. J. D. Connolly and R. McCrindle, J. Chem. Soc. (C), 1966, 1613.
48. Ď. H. R. Barton and N. H. Werstuik, J. Chem. Soc. (C), 1968, 148.
49. H. C. Brown and H. R. Deck, J. Amer. Chem. Soc., 1965, 87, 5620.
50. E. J. Corey, R. Hartmann, and P. A. Vatakencherry, J. Amer. Chem. Soc., 1962, 84, 2611.
51. G. Brieger, Tetrahedron Letters, 1963, 1949.
52. J. Wolinsky, R. L. Marhenke, and R. Lau, Synthetic Communications, 1972, 2, 165.
53. E. J. Corey and M. F. Semmelhack, J. Amer. Chem. Soc., 1967, 89, 2755.
54. E. J. Corey, S. W. Chow, and R. A. Scherrer, J. Amer. Chem. Soc., 1957, 79, 5773.
55. E. Y. Kamat, K. K. Chakravarti, and S. C. Bhattacharyya, Tetrahedron, 1967, 23, 4487.
56. H. Meerwein and K. Van Emster, Ber., 1920, 53, 1815
57. J. W. Powell and M. C. Whiting, Tetrahedron, 1959, 7, 305.
58. E. Piers, R. W. Britton, R. J. Keziere, and R. D. Smiłlie, Canad. J. Chem., 1971, 49, 2620
59. E. Piers, M. B. Geraghty, F. Kido, and M. Soucy, Synth. Comm., 1972, 3, 39
60. M. Kolbe-Haugwitz and L. Westfelt, Ada Chem. Scand., 1970, 24, 1623.
61. Spectral data in agreement with published values: P. de Mayo and R. E. Williams, J. Amer. Chem. Soc., 1965, 87, 3275.
62. A. R. Pinder and R. A. Williams, J. Chem. Soc., 1963, 2773.
63. O. P. Vig, J. M. Sehgal, M. M. Mahajan, and S. D. Sharma, J. Indian Chem. Soc., 1969, 46, 887.
64. M. Julia, S. Julia, and R. Guegan, Bull. Soc. chim. France, 1960, 26, 1072.
65. K. Pihlaja, G. M. Kellie, and F. G. Riddell, J.C.S. Perkin II, 1972, 252.
66. G. C. Joshi, W. D. Chambers, and E. W. Warnhoff, Tetrahedron Letters, 1967, 3613.
67. D. H. R. Barton and N. H. Werstiuk, J. Chem. Soc. (C), 1968, 148