@article{5d420c171cc64e2b8193b01b86db2226,
title = "Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane",
abstract = "Chromium trioxide oxidation of 3β-acetoxy-5α-lanostane (IVa) has been evaluated as a route to 3β-acetoxy-20-oxo-4,4,14α-trimethyl-5α-pregnane (VI) and 3β-acetoxy-17-oxo-4,4,14-α-trimethyl-5α-androstane (VIIa). One of the principal oxidation products was 3β-acetoxy-25-oxo-5α-27-norlanostane (V). Transformation of 25-ketone V to 3β,24-dihydroxy-4,4,14α-trimethyl-5α-cholane (VIIIa) confirmed the structural assignment. Although small amounts of 20-oxo-pregnane VI and 17-oxo-androstane VIIa were detected among the oxidation products, stepwise degradation of lanosterol was considered a more satisfactory route to these substances.",
author = "Pettit, {G. R.} and Alkalay, {D. S.} and P. Hofer and Whitehouse, {P. A.}",
note = "Funding Information: 1 Part XXI, G. R. Pettit, B. Green, A. K. Das Gupta and G. L. Dunn, Ekperientiu,in press. 1 This investigation was supported by PHS Research Grants CY-4074 to CA-04074-06 from the National Cancer Institute, Public Health Service. a For example, refer to: A. Butenandt, H. Bannenbaum, G. Hanisch and H. Kudzsus, 2. Physiol. Chem.2 37, 57 (1935); L. Ruzicka and A. Wettstein, He/u. Chim. Acfa 18, 986 (1935); and E. S Wallis and E. Femholz, J. Amer. Chem.S ot. 57,1504( 1935). Reviews of these studies have been prepared by a H. I. Ruiz, A&es Inst. Farm. fipun. 4, 289 (1955)[ Chem.A bsrr. 51, 6670 (1957)] and b L. F. Fieser and M. Fieser, Steroidsp . 507. Reinhold, New York (1959). Oxidative de-gradation of 3p-acetoxy-Sacholestane to 3/?-acetoxy-17-oxo-5r-androstane, employing CrOs, was reported the preceding year: L. Ruzicka, M. W. Goldberg and H. Briingger, He/u. Chim. Acre 17, 1389 (1934). 4 The first report of these investigations was summarized by W. Schoeller, A. Serini and M. Gehrke, Nururwissenschafte2n3 , 337 (1935) [Chem.A bsstr3. 5,377l (1941)J. s S. P. J. Maas and J. G. DeHeus, Rec. Trao. Chim. 77,531 (1958). 6 C. S. Barnes, D. H. R. Barton, A. R. H. Cole, J. S. Fawcett and B. R. Thomas, J. Chem.S ot. 571 (1953). Related studies leading to the now accepted structure of lanosterol have been sum-marized in an interesting review by E. R. H. Jones and T. G. Halsall, Progressi n the Chemistryo f Organic Natural Products( Edited by L. Zechmeister) Vol. XII; p. 44. Springer-Verlag, Vienna (1955). {\textquoteright} C. S. Barnes, Austr. J. Chem.9, 228 (1956).",
year = "1964",
doi = "10.1016/S0040-4020(01)99176-8",
language = "English (US)",
volume = "20",
pages = "1755--1762",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "7",
}