References
- Dusza , J. P. and Bernstein , S. 1963 . J. Org. Chem. , 28 : 760 Major literature
- Tsuji , A. , Smulowtiz , M. , Liang , J. S. C. and Fukushima , D. K. 1974 . Steroids , 24 : 739
- Thalén , A. and Wickström , L.-I. 1984 . Acta Pharm. Suec. , 21 : 145
- Sweet , F. and Samant , B. R. 1984 . J. Org. Chem. , 49 : 2634
- Draper , R. W. , Berkenkopf , J. , Carlon , E. , Fernandez , X. , Monahan , M. and Lutsky , B. N. 1982 . Arzneim.-Forsch. Drug. Res. , 32 ( I ) : 317
- Zürcher , A. , Heusser , H. , Jeger , O. and Geistlich , P. 1954 . Helv. Chim. Acta , 37 : 1562
- Siddall , J. B. , Marshall , J. P. , Bowers , A. , Cross , A. D. , Edwards , J. A. and Fried , J. H. 1966 . J. Am. Chem. Soc. , 88 : 379
- Furlenmeier , A. , Fürst , A. , Langemann , A. , Waldvogel , G. , Kerb , U. , Hocks , P. and Wiechert , R. 1966 . Helv. Chim. Acta , 49 : 1591
- Kerb , U. , Schulz , G. , Hocks , P. , Wiechert , R. , Furlenmeier , A. , Fürst , A. , Langemann , A. and Waldvogel , G. 1966 . Helv. Chim. Acta , 49 : 1601
- Thompson , M. J. , Robbins , W. E. , Kaplanis , J. N. , Cohen , C. F. and Lancaster , S. M. 1970 . Steroids , 16 : 85
- Shapiro , E. L. , Gentles , M. J. , Tiberi , R. L. , Popper , T. L. , Berkenkopf , J. , Lutsky , B. and Watnick , A. S. 1987 . J. Med. Chem. , 30 : 1581 9α, 21-Dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione, See
- Popper , T. L. , Gentles , M. J. , Kung , T. T. , Berkenkopf , J. , Lutsky , B. N. , Watnick , A. S. and Shapiro , E. L. 1987 . J. Steroid Biochem. , 27 : 837
- In relation to this, the 9α, 11α-oxide 22 was subjected to allylic oxidation (3.0 eq SeO2, dioxane, 100°C, 42 h), but no product was obtained
- Collins , D. J. and Hobbs , J. J. 1963 . Tetrahedron Lett. , : 197 For 6-substituted Δ4–3-ketosteroids
- Okamoto , T. and Kawazoe , Y. 1963 . Chem. Pharm. Bull. , 11 : 643
- In 9β, 11β-oxides, however, the differences were small and irregular, presumably because of B-ring distortion and different degrees of long-range shielding by the oxide ring system, e.g. 1a: δ 4.71 (ddd, 1H, J=10, 5, and 1.5 Hz, 6β-H), 6.48 (t, 1H, J=1.5 Hz, 4-H); 1b: δ 4.50 (ddd, 1H, J=10, 5, and 1.5 Hz, 6α-H), 6.48 (t, 1-H, J=1.5 Hz, 4-H); 7a: δ 4.55 (ddd, 1H, J=10, 5, and 1.5 Hz, 6β-H), 6.50 (t, 1H, J=1.5 Hz, 4-H); 7b: δ 4.42 (t, 1H, J=2 Hz, 6α-H), 6.17 (t, 1H, J=2 Hz, 4-H)
- Details of the X-ray analyses will be reported elsewhere
- Similarly, the 1,2-dihydro derivatives of betamethasone 21-acetate, dexamethasone 17-propionate 21-acetate (3.3 eq SeO2, dioxane, 80°C, 2.5 h), and betamethasone 17,21-dipropionate (3 eq SeO2, dioxane, 110°C, 2.5 h) were converted to the corresponding 6β-alcohols in 22%, 23%, and 25% yields, respectively
- Sharpless , K. B. and Lauer , R. F. 1972 . J. Am. Chem. Soc. , 94 : 7154 If the 6-hydroxylation reaction can be rationalized by assuming initial formation of an ene product, e.g. the 5-ene-4-seleninic acid, followed by its [2,3]-sigmatropic rearrangement, the stereochemistry may be determined by the orientation of the 4-seleninic group first introduced in the ene reaction. See also