Modified steroids: Pb(OAc)4 mediated one-pot multistage transformations of steroidal unsaturated 1,2-diols

Tetrahedron Asymmetry

Volumn 10, Issue 8, 1999, Pages 1527-1537

  Rico Ferreira, Maria Del Rosario ^a   Martín Hernando, José Ignacio ^a   Lena, José Ignacio Candela ^a   Quílez Del Moral, José ^a   Arseniyadis, Siméon ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETIC ACID DERIVATIVE; ACETONITRILE; DEUTERIUM; HOMOSTEROID; TESTOSTERONE;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

EID: 0033597429     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00131-7     Document Type: Article

References (37)

1. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
2. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
3. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
4. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
5. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
6. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
7. 1. A-Homosteroids: Goldberg, M. W.; Kirchensteiner, H. Helv. Chim. Acta 1943, 26, 288; Velgová, H.; Cerny, V.; Sorm, F. Collect. Czech. Chem. Commun. 1973, 38, 2751-2759; B-Homosteroids: Ringold, H. J. J. Am. Chem. Soc. 1960, 82, 961-963; Kohut, L; Fajkos, J.; Sorm, F. Collect. Czech. Chem. Commun. 1967, 32, 1210-1228; Kohut, L. Collect. Czech. Chem. Commun. 1972, 37, 2227-2233; D-Homosteroids: Goldberg, M. W.; Monnier, R. Helv. Chim. Acta 1940, 23, 376, 840; A-nor-B-homosteroids: Suginome, H.; Yabe, T.; Osawa, E. J. Chem. Soc. Perkin Trans. 1 1982, 931-938.
8. 2. 5 α-Reductase is the NADPH-dependent enzyme which irreversibly converts testosterone to the more potent androgen dihydrotestosterone. Anderson, K. M.; Liao, S. Nature. 1968, 219, 277; Imperato-McGinley, J.; Guerro, L.; Gautier, T.; Peterson, R. E. Science 1974, 186, 1213-1215; Bardin, C. W.; Catterall, J. F. Science 1981, 211, 1285.
9. 2. 5 α-Reductase is the NADPH-dependent enzyme which irreversibly converts testosterone to the more potent androgen dihydrotestosterone. Anderson, K. M.; Liao, S. Nature. 1968, 219, 277; Imperato-McGinley, J.; Guerro, L.; Gautier, T.; Peterson, R. E. Science 1974, 186, 1213-1215; Bardin, C. W.; Catterall, J. F. Science 1981, 211, 1285.
10. 2. 5 α-Reductase is the NADPH-dependent enzyme which irreversibly converts testosterone to the more potent androgen dihydrotestosterone. Anderson, K. M.; Liao, S. Nature. 1968, 219, 277; Imperato-McGinley, J.; Guerro, L.; Gautier, T.; Peterson, R. E. Science 1974, 186, 1213-1215; Bardin, C. W.; Catterall, J. F. Science 1981, 211, 1285.
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13. 5. Tetrahedron Symposia-in-Print Number 62, Cascade Reactions, R. Grigg, Ed. 1996, 52, 11385-11664, and references cited therein.
14. 6. Articles dealing with specific aspects of organolead chemistry: for a review on α′-acetoxylation of α,β-unsaturated ketones see: Demir, A. S.; Jeganathan, A. Synthesis 1992, 235-247; for oxidative transformations see: Rubottom, G. M. Oxidation in Organic Chemistry, Part D; Trahanowsky, W. H., Ed.; Academic Press; London, 1982; for carbon-carbon bond forming reactions see: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353-1382.
15. 6. Articles dealing with specific aspects of organolead chemistry: for a review on α′-acetoxylation of α,β-unsaturated ketones see: Demir, A. S.; Jeganathan, A. Synthesis 1992, 235-247; for oxidative transformations see: Rubottom, G. M. Oxidation in Organic Chemistry, Part D; Trahanowsky, W. H., Ed.; Academic Press; London, 1982; for carbon-carbon bond forming reactions see: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353-1382.
16. 6. Articles dealing with specific aspects of organolead chemistry: for a review on α′-acetoxylation of α,β-unsaturated ketones see: Demir, A. S.; Jeganathan, A. Synthesis 1992, 235-247; for oxidative transformations see: Rubottom, G. M. Oxidation in Organic Chemistry, Part D; Trahanowsky, W. H., Ed.; Academic Press; London, 1982; for carbon-carbon bond forming reactions see: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353-1382.
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20. 10. Arseniyadis, S.; Quilez del Moral, J.; Brondi Alves, R.; Potier, P.; Toupet, L. Tetrahedron: Asymmetry 1998, 9, 2871-2878.
21. 11. Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron 1994, 50, 8399-8426.
22. 12. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Criegee, R. Chem. Ber. 1931, 64, 260-266; Rigby, W. J. Chem. Soc. 1950, 1907-1913.
23. 12. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Criegee, R. Chem. Ber. 1931, 64, 260-266; Rigby, W. J. Chem. Soc. 1950, 1907-1913.
24. 12. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Criegee, R. Chem. Ber. 1931, 64, 260-266; Rigby, W. J. Chem. Soc. 1950, 1907-1913.
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26. 14. Arseniyadis, S.; Rodriguez, R.; Cabrera, E.; Thompson, A., Ourisson, G. Tetrahedron 1991, 47, 7045-7058.
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28. 15. Ley, S. V.; Norman, J.; Griflith, W. P.; Marsden, S. P. Synthesis 1994, 639-666; Griffith, W. P.; Ley, S. V. Aldrichimica Acta 1990, 23, 13.
29. + see: Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
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31. + see: Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
32. + see: Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
33. + see: Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
34. + see: Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
35. 17. Arseniyadis, S.; Rico Ferreira, M.; Quilez del Moral, J.; Martin Hernando, J.; Potier, P.; Toupet, L. Tetrahedron: Asymmetry 1998, 9, 4055-4071; Arseniyadis, S.; Rico Ferreira, M.; Quilez del Moral, J.; Martin Hernando, J.; Birlirakis, N.; Potier, P. Tetrahedron: Asymmetry 1999, 10, 193-206.
36. 17. Arseniyadis, S.; Rico Ferreira, M.; Quilez del Moral, J.; Martin Hernando, J.; Potier, P.; Toupet, L. Tetrahedron: Asymmetry 1998, 9, 4055-4071; Arseniyadis, S.; Rico Ferreira, M.; Quilez del Moral, J.; Martin Hernando, J.; Birlirakis, N.; Potier, P. Tetrahedron: Asymmetry 1999, 10, 193-206.
37. 18. Micheli, R. A.; Hajos, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. J. Org. Chem. 1975, 40, 675-679.