Process for preparation of 16 .alpha.-methyl corticoids from .DE

Details Process for preparation of 16 .alpha.-methyl corticoids from .DE Process for preparation of 16 .alpha.-methyl corticoids from .DE

1984-02-27

1985-07-23

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26039745, C07J 700

Patent

active

045307954

ABSTRACT:
This invention discloses a general process for the production of corticoids from respective steroid-type compounds having a double bond from C-16 to C-17. The invention provides a viable alternative synthesis of 17.alpha.-hydroxy-progesterones and like corticoids.

REFERENCES:
patent: 4041055 (1977-08-01), Phephard et al.
patent: 4216159 (1980-08-01), Hessler et al.
VanRheenen, et al., "New Synthesis of Corticosteroids from 17-Keto Steroids: Application and Stereochemical Study of the Unsaturated Sulfoxide-Sulfenate Rearrangement", J. Org. Chem., Communications, vol. 44, No. 9, pp. 1582-1584, (1979).
Redpath, et al., "Stereoselective Synthesis of Steroid Side-Chains", Chemical Society Reviews, vol. 12, No. 1, pp. 75-98, (1983).
Morera, et al., "Preparative and Stereochemical Features of the Sulfoxide-Sulfenate [2,3]Sigmatropic Rearrangement in 17-Vinyl-17-Hydroxy Steroids", J. of Org. Chem., vol. 48, No. 1, pp. 119-121, (1983).
Daniewski, et al., "Synthesis of the Corticoid Side-Chain", J. of Org. Chem., vol. 47, No. 15, pp. 2993-2995, (1982).
Barton, et al., "Efficient Synthesis of the Corticosteroid Side-Chain from 17-Ketones", J. of the Chem. Soc. Chemical Communications, No. 15, pp. 774-775, 1981.
"Steroids", Kirt-Othmer Encyclopedia of Chemical Technology, 2nd Edition, vol. 18, Interscience Publishers, Division of John Wiley and Sons, Inc., (1969), pp. 840-843.
Douglass, et al., "A Superior Method for Preparing Sulfinyl Chlorides", J. Org. Chem., vol. 33, pp. 2104-2106, (1968).
Evans, et al., "Allylic Sulfoxides: Useful Intermediates in Organic Synthesis", Accounts of Chemical Research, vol. 7, 147-155, (1974).
Djerassi, Steroid Reactions an Outline for Organic Chemists, Chapter 1, by Keana, pp. 1-87, Holden-Day, Inc., San Francisco, (1963).

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