Sterol synthesis. A simplified method for the synthesis of 32-oxygenated derivatives of 24,25-dihydrolanosterol.

Bloch, 1965, The biological synthesis of cholesterol, Science., 150, 19, 10.1126/science.150.3692.19

Clayton, 1965, Biosynthesis of sterols, steroids, and terpenoids. Part I. Biogenesis of cholesterol, Quart. Rev., 19, 168, 10.1039/qr9651900168

Frantz, 1967, Sterol biosynthesis, Ann. Rev. Biochem., 36, 691, 10.1146/annurev.bi.36.070167.003355

Fried, 1968, Enzymatic conversion of 32-oxygenated Δ7-lanosterol derivatives and of Δ8(14)-4,4-dimethyl-cholestenol to cholesterol, Biochem. Biophys. Res. Commun., 32, 568, 10.1016/0006-291X(68)90701-8

Schroepfer, 1972, Recent investigations on the nature of sterol intermediates in the biosynthesis of cholesterol, Proc. R. Soc. London Ser. B., 180, 125, 10.1098/rspb.1972.0010

Gaylor, 1973, Investigation of the multienzymic system of microsomal cholesterol biosynthesis, Ann. N. Y. Acad. Sci., 212, 122, 10.1111/j.1749-6632.1973.tb47591.x

Gibbons, 1976, Lanosterol 14α-demethylase. The metabolism of some potential intermediates by cell-free systems from rat liver, Biochem. Biophys. Res. Commun., 69, 781, 10.1016/0006-291X(76)90943-8

Akhtar, 1978, Chemical and enzymic studies on the characterization of intermediates during the removal of the 14α-methyl group in cholesterol biosynthesis, Biochem. J., 169, 449, 10.1042/bj1690449b

Pascal, 1980, Concerning possible mechanisms of demethylation of 14α-methyl sterols in cholesterol biosynthesis, J. Am. Chem. Soc., 45, 4034

Schroepfer, 1978, Inhibition of sterol biosynthesis by 14α-hydroxymethyl sterols, Biochem. Biophys. Res. Commun., 83, 1024, 10.1016/0006-291X(78)91498-5

Gibbons, 1980, Regulation of cholesterol biosynthesis in cultured cells by probable natural precursor sterols, J. Biol. Chem., 255, 394, 10.1016/S0021-9258(19)86186-0

Schroepfer, 1980, Inhibition of sterol biosynthesis in animal cells by 14α-hydroxymethyl sterols, J. Lipid Res., 21, 571, 10.1016/S0022-2275(20)42227-8

Fried, 1965, 32-Oxygenated lanostane derivatives from 3β-acetoxy-Δ7-anostene via 7α,8α-epoxides, Tetrahedron Lett., 2499, 10.1016/S0040-4039(01)84013-2

Knapp, 1976, Mass spectral fragmentation of 5α-hydroxy-steroids, Chem. Phys. Lipids., 16, 31, 10.1016/0009-3084(76)90013-X

Knapp, 1976, Mass spectrometry of sterols. Electron ionization induced fragmentation of C-4-alkylated cholesterols, Chem. Phys. Lipids., 17, 466, 10.1016/0009-3084(76)90048-7

Schroepfer, 1979, Inhibition of sterol synthesis in animal cells by 15-oxygenated sterols with the unnatural cis-C-D ring junction–-5α,14β-cholest-7-en-15α-ol-3-one and 5α,14β-cholest-7-en-15β-ol-3-one, Biochem. Pharmacol., 28, 249, 10.1016/0006-2952(79)90511-2

Knapp, 1975, Chemical synthesis, spectral properties and chromatography of 4α-methyl and 4β-methyl isomers of (24R)-24-ethyl-5α-cholestan-3β-ol and (24S)-24-ethyl-cholesta-5,22-dien-3β-ol, Steroids., 26, 339, 10.1016/0039-128X(75)90079-3

Zurcher, 1963, Protoneureson anz spektroskopic und Steroidstruktur II, Helv. Chem. Acta., 46, 2054

Marker, 1937, Sterols. XVI. Lanosterol and agnosterol., J. Am. Chem. Soc., 59, 1368, 10.1021/ja01286a061

Fieser, 1959, 365

Gaylor, 1963, Biosynthesis of skin sterols. IV. Identification of labeled lanosta-7,24-dien-3β-ol from rat skin, J. Biol. Chem., 238, 1649, 10.1016/S0021-9258(18)81116-4

Knight, 1967, Steroids and related natural products. Part XLII. 14α-Methyl cholestanes, J. Chem. Soc., 2427

Pascal, 1979, Chemical synthesis of three 14α-hydroxymethyl cholestenols, J. Lipid Res., 20, 570, 10.1016/S0022-2275(20)40578-4

Brown, 1970, Additions to bicyclic olefins. IV . The facile reduction of labile epoxides of bicyclic olefins by lithium in ethylenediamine, J. Org. Chem., 35, 3243, 10.1021/jo00835a013

Barton, 1953, Triterpenoids. Part XII. The lanosterol analogue of provitamin D3, J. Chem. Soc., 1842, 10.1039/jr9530001842

Fried, 1965, Transformations of eburicoic acid. VI. 9α-Hydroxy-lanostane and eburicane derivatives and their photolytic fragmentation to 9,10-secosteroids, Tetrahedron Lett., 849, 10.1016/S0040-4039(00)90029-7

Guest, 1971, Steroids. Part XIV. Transformations of 8α,9α- and 9α,11α-epoxy-lanostanes and related compounds, J. Chem. Soc. C., 1468, 10.1039/J39710001468

Batten, 1972, The synthesis of some 32-functionalized lanostane derivatives, J. Chem. Soc. Perkin I., 739, 10.1039/p19720000739

Akhtar, 1977, The pathway for the removal of the 15α-methyl group of lanosterol. The role of lanost-8-ene-3β,32-diol in cholesterol biosynthesis, Bioorg. Chem., 6, 473, 10.1016/0045-2068(77)90046-3

Fried, 1966, 32-Hydroxylated lanostane derivatives by photolysis of 3β-acetoxy-7-ketolanostane, Tetrahedron Lett., 1677, 10.1016/S0040-4039(01)99776-X

Bentley, 1965, The synthesis of 32-oxygenated lanostane derivatives, Tetrahedon Lett., 2497, 10.1016/S0040-4039(01)84012-0

Allen, 1973, Nitrite photolysis in the presence of oxygen. An improved synthesis of 32-oxygenated lanostanes, J. Chem. Soc. Perkin I., 2402, 10.1039/p19730002402

Barton, 1979, The mechanism of the Barton reaction, J. Chem. Soc. Perkin I., 1159, 10.1039/p19790001159

Ruzicka, 1944, 55. Zur Kenntnis der Triterpene. Uber verschiedene Umwandlungsprodukte des Lanosterins, Helv. Chim. Acta., 27, 472, 10.1002/hlca.19440270158

Birchenough, 1950, Lanosterol. Part IX. Ketodihydrolanosterol, J. Chem. Soc., 1249, 10.1039/jr9500001249

Barton, 1951, Triterpenoids. Part IV. Some observations on the constitution of lanostadienol (lanosterol), J. Chem. Soc., 3147, 10.1039/jr9510003147

Shoppe, 1968, Steroids. Part XXXI. Attempted modification of the 14α-methyl group in 4,4,14α-trimethyl steroids, J. Chem. Soc. C., 1581, 10.1039/J39680001581

Lassak, 1973, The two C8 epimers of 3β-acetoxylanost-9(11)-en-7-one, Aust. J. Chem., 26, 1051, 10.1071/CH9731051