19-hydroxy-5β,19-cyclosteroids: Synthesis, isomerization and ring opening

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 12, 1997, Pages 1895-1904

  Templeton, John F ^a   Ling, Yangzhi ^a   Lin, Weiyang ^a   Majgier Baranowska, Helena ^a   Marat, Kirk ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748620330     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a604405k     Document Type: Article

References (32)

1. J. F. Templeton, Y. Ling, W. Lin, R. J. Pitura and K. Marat, J. Chem. Soc., Perkin Trans. 1, 1994, 1149.
2. J. F. Templeton, W. Lin, Y. Ling and K. Marat, Tetrahedron Lett., 1994, 35, 5755.
3. J. C. Orr, J. F. Templeton, H. Majgier-Baranowska and K. Marat, J. Chem. Soc., Perkin Trans. 1, 1994, 2667.
4. L. Tin in Frontiers in Biotransformation, ed. K. Ruckpaul and H. Rein, Akademia Verlag, Berlin, 1992, vol. 6, pp. 1001-101.
5. H. Laurent and R. Weichert in Organic Reactions in Steroid Chemistry, ed. J. Fried and J. A. Edwards, Van Nostrand Reinhold Co., New York, 1972, vol. 2, pp. 110-113.
6. A. J. Birch and G. S. R. Subba Rao, J. Chem. Soc., 1965, 5139.
7. S. Rakhit and M. Gut, J. Am. Chem. Soc., 1964, 86, 1432.
8. J. J. Bonet, H. Werhli and K. Schaffner, Helv. Chim. Acta, 1962, 45, 2615.
9. J. Tadanier and W. Cole, Tetrahedron Lett., 1964, 1345.
10. L. H. Knox, E. Blossey, H. Carpio, L. Cervantes, P. Crabbe, E. Velarde and J. A. Edwards, J. Org. Chem., 1965, 30, 2198.
11. E. Santaniello and E. Caspi, J. Steroid Biochem., 1976, 7, 223.
12. R. L. Dyer and T. A. Harrow, Steroids, 1979, 33, 617.
13. H. L. Holland and G. J. Taylor, Can. J. Chem., 1978, 56, 3121.
14. L. H. Knox, E. Velarde and A. D. Cross, J. Am. Chem. Soc., 1963, 85, 2533;
15. L. H. Knox, E. Velarde, S. Berger, D. Cuadriello and A. D. Cross, Tetrahedron Lett., 1962, 1213.
16. P. Wieland and G. Anner, Helv. Chim. Acta, 1968, 51, 1932;
17. P. Wieland and G. Anner, Helv. Chim. Acta, 1970, 53, 116.
18. K. Marat, J. F. Templeton, Y. Ling, W. Lin and R. K. Gupta, Magn. Res. Chem., 1995, 33, 529.
19. E. Wenkert and E. Kariv, Chem. Commun., 1965, 570;
20. E. Kariv and E. Wenkert, Israel J. Chem., 1967, 5, 68.
21. W. Reusch, K. Grimm, J. E. Karoglan, J. Martin, K. P. Subrahamanian, Y. C. Toong, P. S. Venkataramani, J. D. Yordy and P. Zoutendam, J. Am. Chem. Soc., 1977, 99, 1953 and references therein.
22. N. H. Werstiuk, Tetrahedron, 1983, 39, 205.
23. W. Reusch, K. Grimm, J. E. Karoglan, J. Martin, K. P. Subrahamanian, P. S. Venkataramani and J. D. Yordy, J. Am. Chem. Soc., 1977, 99, 1958.
24. D. H. Gibson and C. H. DePuy, Chem. Rev., 1974, 74, 605.
25. J. W. Blunt and J. B. Stothers, Org. Magn. Res., 1977, 9, 439.
26. A. M. H. Brodie, W. C. Schwarzel, A. A. Shaikh and H. J. Brodie, Endocrinology, 1977, 100, 1684;
27. J. F. Templeton, Y. Ling, W. Lin, R. J. Pitura, H. Majgier-Baranowska and A. M. H. Brodie, The IV International Aromatase Conference, June 7-11, 1996 Tahoe City, Tahoe, California, USA.
28. D. M. Doddrell, D. P. Pegg and M. T. Bendall, J. Magn. Reson., 1982, 48, 323.
29. H. Hagiwara, S. Noguchi and M. Nishikawa, Chem. Pharm. Bull., 1960, 8, 84.
30. H. Ueberwasser, K. Heusler, J. Kalvoda, C. Meystre, P. Wieland, G. Anner and A. Wettstein, Helv. Chim. Acta, 1963, 34, 343.
31. A. L. Wilds and N. A. Nelson, J. Am. Chem. Soc., 1953, 75, 5366.
32. Y. Ito, T. Hirao and T. Saeguse, J. Org. Chem., 1978, 43, 1011.