Abstract
Epoxidation of Δ5-steroids with a potassium permanganate and a range of metal salts in the solid phase gives the 5β, 6β-epoxides. The results have been rationalised in terms of the oxophilic metal ions favouring epoxide formation in the collapse of a manganate intermediate.
References
1.
Glotter E.
, Natural Product Reports , 1991 , 8 , 415 .
2.
Bingham K.D.
,
Blaiklock T.M.
,
Coleman R.C.B.
and
Meakins G.D.
, J. Chem. Soc.(C) 1 1970 , 2330.
3.
Bovicelli P.
,
Lupattelli P.
,
Mincione E.
,
Prencipe T.
and
Curci R.
, J. Org. Chem. , 1992 , 57 , 2182 .
4.
Syamala M.S.
,
Das J.
,
Baskaran S.
and
Chandrasekaran S.
, J. Org. Chem. , 1992 , 57 , 1928 .
5.
Hansoni
J.R.
Hitchcock
P.B.
,
Liman M.D.
,
Nagaratnam S.
and
Manickavasagar R.
, J. Chem. Research (S), 1995 , 220.
6.
Parish E.J.
,
Li H.
and
Li S.
, Synth. Commun. , 1995 , 25 , 927 .
7.
Salvador
J.A.R.
,
Sa e Melo
M.L.
and
Campos Neves
A.S.
, Tetrahedron Lett.1 1996 , 37 , 687 .
8.
Hanson J.R.
,
Nagaratnam S.
and
Stevens J.
, J. Chem. Res. (8), 1996 , 102.
9.
Parish E.J.
and
Li S.
, J. Chem. Res. (S), 1996 288.
10.
Parish E.J.
and
Li S.
, J. Org. Chem.1 1996 , 61 , 5665 .
11.
Wiberg K.B.
and
Saegebarth K.A.
, J. Am. Chem. Soc. , 1957 , 79 , 2822 .
12.
Fatiadi A.J.
, Synthesis1 1987 , 85.
13.
Ruzicka L.
and
Muhr A.C.
, Helv. Chim. Acta , 1944 , 27 , 503 .
14.
Plattner P.A.
,
Petrzilka T.
and
Lang W.
, Helv. Chim. Acta , 1944 , 27 , 513 .
15.
Akhtar M.
and
Barton D.H.R.
, J. Am. Chem. Soc., 1964 , 86 , 1528 .