The oxidation of steroidal alkenes by potassium permanganate and metal salts in the solid phase gives epoxides with a stereochemistry that can differ from that obtained by the use of per-acids.
FatiadiA.J., Synthesis, 1987, 85; L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Chichester, 1995, vol.6, p.4274
2.
see, for example, ColemanJ.E., RicciutiC., and SwernD., J. Am., Chem. Soc., 1956, 78, 5342.
3.
RobinsonG.M., and RobinsonR., J. Chem. Soc., 1925, 127, 175.
4.
LapworthA., and MottramE. N., J. Chem. Soc., 1925, 127, 1628.
5.
EllisB., and PetrowV., J. Chem. Soc., 1939, 1078; R.E. Marker and E. Rohmann, J. Am. Chem. Soc., 1940, 62, 516.
6.
FieserM., QuilicoA., NickonA., RosenW. E., TarltonE. J., and FieserL. F., J. Am. Chem. Soc., 1953, 75, 4066; see also M. Anastasia, A. Fiecchi and A. Scala, Tetrahedron Lett., 1979, 3323.
7.
SinghH., and PaulD., J. Chem. Soc. Perkin Trans.l, 1974, 1475; A.P. King and R.E. Benson, Org. Synth. Coll. Vol. VI, 1988, 690.
8.
NaceH.R., and RiegerA. L., J. Org. Chem., 1970, 35, 3846.
9.
GokelG.W., and DurstH. D., Synthesis, 1976, 168; Angew. Chem. Int. Ed. Engl. 1979, 18, 787
10.
BushenV., RathoreR., and ChandrasekaranS., Synthesis, 1984, 431.
11.
SamD.J., and SimmonsH. F., J. Am. Chem. Soc., 1972, 94, 4024; 1974, 96, 2252.
12.
WibergK.B., and SaegebarthK. A., J. Am. Chem. Soc., 1957, 79, 2822.
13.
LaiS., and LeeD. G., Tetrahedron, 2002, 58, 9879.
14.
RegenS.L., and KoteelC. J., J. Am. Chem. Soc., 1977, 99, 3837.
15.
ClarkH.J., and CorkD. G., J. Chem. Soc., Chem. Commun.1982, 635.
16.
MengerF.M., and LeeC., J. Org. Chem., 1979, 44, 3446.
17.
JeffordC.W., and WangY., J. Chem. Soc. Chem. Commun., 1988, 634.
18.
NoureldinN.A., McConnellW. B., and LeeD. G., Canad. J. Chem., 1984, 62, 2113.
19.
LeeD.G., and NoureldinN. A., J. Am. Chem. Soc., 1983, 105, 3188.
20.
BaskaranS., DasJ., and ChandrasekaranS., J. Org. Chem., 1989, 54, 5182.
