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Abstract

The epoxidation of 6β-acetoxyandrosta-2,4-diene-17-one, 6β-acetoxypregna-2,4-diene-20-one and the corresponding 6-ketones with m-chloroperbenzoic acid is shown to give, unexpectedly, the 4α,5α-monoepoxides.

References

S. S.

and Robinson

C. H.

, J. Steroid Biochem. Mol. Biol., 1993, 44, 389.

S. S.

and Robinson

C. H.

, J. Chem. Soc., Perkin Trans. 1, 1994, 2237.

Bergmann

and Skau

E. L.

, J. Org. Chem., 1940, 5, 439.

Cerny

, Hudesinsky

, Ryba

and Turecek

, Collect. Czech. Chem. Commun., 1988, 5, 1549.

Hanson

J. R.

and Kiran

, J. Chem. Res. 1999, (S) 594; (M) 2532.

Hanson

J. R.

and Organ

T. D.

, J. Chem. Soc., Perkin Trans. 1, 1970, 2473.

Knof

, Liebigs Ann. Chem., 1962, 657, 171.

Hanson

J. R.

and Shapter

H. J.

, J. Chem. Soc., Perkin Trans. 1, 1972, 1445.

Rakhit

and Gut

, J. Org. Chem., 1968, 33, 1196.

10.

de Paulet

A. Crastes

and Bascoul

, Bull. Soc. Chim. Fr., 1966, 939.

The Epoxidation of Androstane and Pregnane 2,4-Dienes

Abstract

References