Chromyl acetate and chromyl trifluoroacetate are effective reagents for the oxidation of C-25 on cholestane side-chains to the corresponding C-25 hydroxy derivative.
References
1.
BreslowR. and MeyerD., J. Am. Chem. Soc., 1982, 104, 2046.
2.
BreslowR., Acc. Chem. Res., 1980, 13, 170.
3.
BreslowR., CorcoranR. J., SniderB. B., DollR. J., KhannaP. L. and KaleyaR., J. Am. Chem. Soc., 1977, 99, 905.
4.
SniderB. B., CorcoranR. J. and BreslowR., J. Am. Chem. Soc., 1975, 97, 6580.
5.
BreslowR., CorcoranR., DaleJ. A., LiuS. and KilickyP., J. Am. Chem. Soc., 1974, 98, 1973.
6.
ParishE. J., ParishS. C. and LiS., Lipids, 1995, 30, 247.
7.
SpenselT. A., Acc Chem. Res., 1994, 27, 83.
8.
TaylorF. R., in Regulation of Isopentenoid Metabolism, ACS Symp. Ser. 497, ed. NesW. D. and ParishE. J., American Chemical Society, Washington, D.C., 1992, pp. 81–93.
9.
KircherH. W. and RosenteinF. U., J. Org. Chem., 1987, 52, 2586 and references therein.
10.
BergmannW. and DuszaJ. P., J. Org. Chem., 1958, 23, 459.
11.
FagerlundU. H. M. and IdlerD. R., J. Am. Chem. Soc., 1957, 79, 6473.
12.
TomkinsonC. O., WilsonT. M., RusselJ. S. and SpencerT. A., J. Org. Chem., 1998, 63, 9919.
13.
DaniniS. R., GuptaA., SextonR. C., ParishE. J. and RudneyH., J. Biol. Chem., 1987, 262, 14435.
14.
SmithL. L., Cholesterol Autooxidation, Plenum Press, New York, 1981 and references therein.
15.
BechwithA. L. J., BodkinC. L. and DoungT.. Aust. J. Chem., 1977, 30, 2177.
16.
CohenZ. and MazurY., J. Org. Chem., 1979, 44, 2318.
17.
BartonD. H. R., BoivinJ. and LelandaisD., J. Chem. Soc., Perkin Trans. 1, 1989, 463.
18.
OritoK., SatohS. and SuginomeH., J. Chem. Soc., Chem. Commun., 1984, 1829.
19.
GrovesJ. T. and NevmannR., J. Org. Chem., 1988, 53, 3891.
20.
BovicelliP., GumibacortaA., LupattelliP. and MincimeB., Tetrahedron Lett., 1992, 33, 7411.
21.
BovicelliP., LupattelliP., in cioneE. M, PrencipeT. and CurciR., J. Org. Chem., 1992, 57, 5052.
22.
KellyR. W. and SykesP. J., J. Chem. Soc., Chem. Commun., 1968, 416.
23.
BinghamR. C. and SchleyerP. V; R., J. Org. Chem., 1971, 36, 1198.
24.
SuggsJ. W. and YtuarteL., Tetrahedron Lett., 1986, 27, 437.
25.
SykesP. J. and KellyR. W., J. Chem. Soc., 1968, 2346.
26.
ParishE. J., ChitrakornS., TaylorF. R. and SavcierS. E., Chem. Phys. Lipids, 1984, 36, 179.