Stereoselectivity of directed epoxidations of 22-hydroxy-Δ23-sterol side chains

Canadian Journal of Chemistry

Volumn 74, Issue 10, 1996, Pages 1857-1867

  Back, Thomas G ^a   Baron, Denise L ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

22 hydroxy 23 sterols; Allylic alcohols; Brassinosteroids; Diastereoselectivity; Epoxidation

Indexed keywords

BINDING ENERGY; CATALYSIS; CATALYST SELECTIVITY; CONFORMATIONS; CROSSLINKING; ISOMERIZATION; MOLECULAR STRUCTURE; OXIDATION; SYNTHESIS (CHEMICAL);

ALLYLIC ALCOHOLS; BRASSINOSTEROIDS; DIASTEREOSELECTIVITY; EPOXIDATION; STEROLS;

FATTY ACIDS;

BRASSICASTEROL; CHOLESTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; EPOXIDATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030272052     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-208     Document Type: Article

References (66)

1. (a) J. Redpath and F.J. Zeelen. Chem. Soc. Rev. 12, 75 (1983);
2. (b) D.M. Piatak and J. Wicha. Chem. Rev. 78, 199 (1978).
3. M.D. Grove, G.F. Spencer, W.K. Rohwedder, N. Mandava, J.F. Worley, J.D. Warthen, Jr., G.L. Steffens, J.L. Flippen-Anderson, and J.C. Cook, Jr. Nature (London), 281, 216 (1979).
4. H. G. Cutler, T. Yokota, and G. Adam (Editors). Brassinosteroids: chemistry, bioactivity and applications. ACS Symp. Ser. 474, Washington, D.C. 1991.
5. T.G. Back. In Studies in natural products chemistry. Vol. 16. Edited by Atta-ur-Rahman. Elsevier, Amsterdam. 1995. pp. 321-364, and references cited therein.
6. (a) S. Fung and J.B. Siddall. J. Am. Chem. Soc. 102, 6580 (1980);
7. (b) S. Takatsuto, N. Yazawa, M. Ishiguro, M. Morisaki, and N. Ikekawa. J. Chem. Soc. Perkin Trans. 1, 139 (1984);
8. (c) S. Takatsuto and N. Ikekawa. J. Chem. Soc. Perkin Trans. 1, 439 (1984);
9. (d) J. Chem. Soc. Perkin Trans. 1, 2269 (1986);
10. (e) Y. Hirano, S. Takatsuto, and N. Ikekawa. J. Chem. Soc. Perkin Trans. 1, 1775 (1984);
11. (f) S. Takatsuto. J. Chem. Soc. Perkin Trans. 1, 1833 (1986);
12. (g) K. Mori and T. Takeuchi. Liebigs Ann. Chem. 815 (1988);
13. (h) K. Mori, M. Sakakibara, and K. Okada. Tetrahedron, 40, 1767 (1984);
14. (i) K. Mori, M. Sakakibara, Y. Ichikawa, H. Ueda, K. Okada, T. Umemura, G. Yabuta, S. Kuwahara, M. Kondo, M. Minobe, and A. Sogabe. Tetrahedron, 38, 2099 (1982);
15. (j) M. Aburatani, T. Takeuchi, and K. Mori. Agric. Biol. Chem. 50, 3043 (1986);
16. (k) M. Sakakibara and K. Mori. Agric. Biol. Chem. 48, 745 (1984);
17. (l) Agric. Biol. Chem. 47, 1407 (1983);
18. (m) T.G. Back, P.G. Blazecka, and M.V. Krishna. Tetrahedron Lett. 32, 4817 (1991);
19. (n) T.G. Back and M.V. Krishna. J. Org. Chem. 56, 454 (1991);
20. (o) H. Hayami, M. Sato, S. Kanemoto, Y. Morizawa, K. Oshima, and H. Nozaki. J. Am. Chem. Soc. 105, 4491 (1983);
21. (p) V.A. Khripach, V.N. Zhabinskiy, and V.K. Olkhovick. Tetrahedron Lett. 31, 4937 (1990);
22. (q) V.A. Khripach. Pure Appl. Chem. 62, 1319 (1990);
23. (r) W.-S. Zhou and L.-F. Huang. Tetrahedron, 48, 1837 (1992);
24. (s) W.-S. Zhou, B. Jiang, and X. Pan. Tetrahedron, 46, 3173 (1990);
25. (t) S. Zheng-Wu and Z. Wei-Shan. J. Chem. Soc. Perkin Trans. 1, 1765 (1990);
26. (u) W.-S. Zhou. Pure Appl. Chem. 61, 431 (1989);
27. (v) B.G. Hazra, P.L. Joshi, B.B. Bahule, N.P. Argade, V.S. Pore, and M.D. Chordia. Tetrahedron, 50, 2523 (1994);
28. (w) B.G. Hazra, N.P. Argade, and P.L. Joshi. Tetrahedron Lett. 33, 3375 (1992);
29. (x) T. Takahasi, A. Ootake, H. Yamada, and J. Tsuji. Tetrahedron Lett. 26, 69 (1985).
30. T.G. Back, P.G. Blazecka, and M.V Krishna. Can. J. Chem. 71, 156 (1993).
31. H.B. Henbest and R.A.L. Wilson. J. Chem. Soc. 1958 (1957).
32. (a) A.H. Hoveyda, D.A. Evans, and G.C. Fu. Chem. Rev. 93, 1307 (1993);
33. (b) A.S. Rao. In Comprehensive organic synthesis. Vol. 7. Edited by B.M. Trost. Pergamon Press, Oxford. 1991. Chap. 3.1;
34. (c) A.S. Rao, S.K. Paknikar, and J.G. Kirtane. Tetrahedron, 39, 2323 (1983);
35. (d) K.B. Sharpless and T.R. Verhoeven. Aldrichimica Acta, 12, 63 (1979).
36. (a) R.A. Johnson and K.B. Sharpless. In Comprehensive organic synthesis. Vol. 7. Edited by B.M. Trost. Pergamon Press, Oxford, 1991. Chap. 3.2;
37. (b) B.E. Rossiter. In Asymmetric Synthesis. Vol. 5. Edited by J.D. Morrison. Academic Press, Orlando, Fla. 1985. Chap. 7;
38. (c) M.G. Finn and K.B. Sharpless. In Asymmetric Synthesis. Vol. 5. Edited by J.D. Morrison. Academic Press, Orlando, Fla. 1985. Chap. 8.
39. M.L. Sassiver and J. English. J. Am. Chem. Soc. 82, 4891 (1960).
40. P. Chamberlain, M.L. Roberts, and G.H. Whitham. J. Chem. Soc. (B), 1374 (1970).
41. P. Chautemps and J.-L. Pierre. Tetrahedron 32, 549 (1976).
42. B.E. Rossiter, T.R. Verhoeven, and K.B. Sharpless. Tetrahedron Lett. 4733 (1979).
43. E.D. Mihelich. Tetrahedron Lett. 4729 (1979).
44. A.S. Narula. Tetrahedron Lett. 22, 2017 (1981).
45. E. Erdik. Tetrahedron, 40, 641 (1984).
46. E.J. Corey and R.A.E. Winter. J. Am. Chem. Soc. 85, 2677 (1963).
47. M.P. Zimmerman, H. Li, W.L. Duax, C.M. Weeks, and C. Djerassi. J. Am. Chem. Soc. 106, 5602 (1984).
48. L. Dai, B. Lou, Y. Zhang, and G. Guo. Tetrahedron Lett. 27, 4343 (1986).
49. R. Monahan, D. Brown, L. Waykole, and D. Liotta. In Organoselenium chemistry. Edited by D. Liotta. Wiley, New York. 1987. Chap. 4.
50. S. Takatsuto, N. Yazawa, and N. Ikekawa. Phytochemistry, 23, 525 (1984).
51. W.C. Still, M. Kahn, and A. Mitra. J. Org. Chem. 43, 2923 (1978).
52. S.D. Young, and W.T. Borden. J. Org. Chem. 45, 724 (1980).
53. B. Méchin and N. Naulet. J. Organomet. Chem. 39, 229 (1972).
54. W.A. Kinney, M.J. Coghlan, and L.A. Paquette. J. Am. Chem. Soc. 107, 7352 (1985).
55. W.G. Kofron and L.M. Baclawski. J. Org. Chem. 41, 1879 (1976).
56. S.C. Watson and J.F. Eastham. J. Organomet. Chem. 9, 165 (1967).
57. M.R. Winkle, J.M. Lansinger, and R.C. Ronald. J. Chem. Soc. Chem. Commun. 87 (1980).
58. (a) J.A. Steele and E. Mosettig. J. Org. Chem. 28, 571 (1963);
59. (b) J.J. Pappas, W.P. Keaveney, E. Gancher, and M. Berger. Tetrahedron Lett. 4273 (1966);
60. (c) R.F.N. Hutchins, M.J. Thompson, and J.A. Svoboda. Steroids, 15, 113 (1970);
61. (d) W.G. Salmond and M.C. Sobala. Tetrahedron Lett. 1695 (1977);
62. (e) J.R. Wiersig, N. Waespe-Sarcevic, and C. Djerassi. J. Org. Chem. 44, 3374 (1979).
63. K. Hiroi and S. Sato. Synthesis, 635 (1985).
64. R.D. Walkup, G.D. Anderson, and C. Djerassi. Tetrahedron Lett. 767 (1979).
65. Y. Fujimoto, M. Kimura, F.A.M. Khalifa, and N. Ikekawa. Chem. Pharm. Bull. 32, 4372 (1984).
66. V.A. Khripach, V.N. Zhabinskii, and E.V. Zhernosek. Tetrahedron Lett. 36, 607 (1995).