4,5-Epoxycholestane-3,6-diols: Templates for generating the full set of eight cholestane-3,5,6-triol stereoisomers in multigram scales, but not for a cholestane-3,4,6-triol

Steroids

Volumn 72, Issue 1, 2007, Pages 95-104

  Zhao, Kejun ^a,b   Wang, Yongfeng ^a   Han, Li ^a  

^a ASTON UNIVERSITY   (United Kingdom)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

4,5 Epoxycholestane 3,6 diols; Cholestane 3,4,6 triol; Cholestane 3,5,6 triol; Epoxide cleavage; Lewis acid; LiAlH4 reduction

Indexed keywords

5ALPHA CHOLESTANE 3ALPHA,5,6ALPHA TRIOL; 5ALPHA CHOLESTANE 3ALPHA,5,6BETA TRIOL; 5ALPHA CHOLESTANE 3BETA,5,6ALPHA TRIOL; 5ALPHA CHOLESTANE 3BETA,5,6BETA TRIOL; 5BETA CHOLESTANE 3ALPHA,5,6ALPHA TRIOL; 5BETA CHOLESTANE 3ALPHA,5,6BETA TRIOL; 5BETA CHOLESTANE 3BETA,5,6ALPHA TRIOL; 5BETA CHOLESTANE 3BETA,5,6BETA TRIOL; ETHYLENEDIAMINE; LEWIS ACID; LITHIUM DERIVATIVE; OXYSTEROL; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; STEREOCHEMISTRY; STEREOISOMERISM; STEROL SYNTHESIS; STRUCTURE ANALYSIS;

CHOLESTANES; CHOLESTANOLS; CHOLESTEROL; HYDROXYCHOLESTEROLS; MASS SPECTROMETRY; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 33845933692     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.11.015     Document Type: Article

References (33)

1. Schroepfer Jr. G.J. Oxysterols: modulators of cholesterol metabolism and other processes. Physiol Rev 80 (2000) 361-554
2. Breuer O., Dzeletovic S., Lund E., and Diczfalusy U. The oxysterols cholest-5-ene-3β,4α-diol, cholest-5-ene-3β,4β-diol and cholestane-3β,5α,6α-triol are formed during in vitro oxidation of low density lipoprotein, and are present in human atherosclerotic plaques. BBA-Lipids Lipid Metab 1302 (1996) 145-152
3. Rueda A., Zubía E., Ortega M.J., and Salvá J. Structure and cytotoxicity of new polyhydroxylated sterols from the Caribbean gorgonian Plexaurella grisea. Steroids 66 (2001) 897-904
4. Zhao K.J., Wang Y.F., and Billington D.C. A multigram preparative synthesis of cholest-4-en-3α,6β- and -3α,6α-diols. Synth Commun 31 (2001) 2619-2624
5. Zhao K.J., Wang Y.F., and Billington D.C. Studies on stereocontrolled epoxidations of bis-alicyclic alcohols in steroidal skeletons: preparation of eight diastereomerically pure epoxides from cholest-4-en-3β,6β-; 3β,6α-; 3α,6β- and -3α,6α-diols. Tetrahedron: Asym 12 (2001) 1211-1217
6. Kimura M., Kawata M., and Sawaya T. Autoxidation of cholesterol in aqueous colloidal dispersions with different detergents. Chem Pharm Bull 24 (1976) 2258-2261
7. Mcquillin I.J., and Ord W.O. Mechanism of hydrogenation. Part II. Acid catalysis of hydrogenolysis of epoxides of allyl alcohol derivatives. J Chem Soc (1959) 3169-3172
8. Rowland A.T. An attempted Westphalen rearrangement of a 5β-hydroxy steroid. J Org Chem 29 (1964) 222-224
9. Bowers A., Denot E., Sánchez M.B., Sánchez-Hidalgo L.M., and Ringold H.J. Steroids. CXXIV. Studies in cyano steroids. Part I. The synthesis of a series of C-6-cyano steroid hormones. J Am Chem Soc 81 (1959) 5233-5242
10. Coxon J.M., Hartshorn M.P., and Lane G.A. NMR spectra of some 3,6-disubstituted-5α-oxygenated cholestanes. Tetrahedron 26 (1970) 841-844
11. Fudge A.J., Shoppee C.W., and Summers G.H.R. Steroids. Part VII. Some 5-hydroxy derivatives of cholestane. J Chem Soc (1954) 958-964
12. Brown H.C., and Yoon N.M. The borohydride-catalyzed reaction of diborane with epoxides. The anti-Markovnikov opening of trisubstituted epoxides. J Am Chem Soc 90 (1968) 2686-2688
13. Wheeler D.M.S., and Wheeler M.M. In: Fried J., and Edwards J.A. (Eds). Reduction of steroidal ketones: organic reactions in steroid chemistry (1972), Van Nostrand Reinhold Company, New York
14. Hudlicky M. Reduction in organic chemistry (1984), Ellis Horwood, Chichester p. 83-87
15. Ashby E.C., and Prather J. The composition of "mixed hydride" reagents. A study of the Schlesinger reaction. J Am Chem Soc 88 (1966) 729-733
16. Lansbury P.T., Scharf D.J., and Pattison V.A. Alane reductions of 1-phenylcyclopentene oxide. J Org Chem 32 (1967) 1748-1751
17. March J. Advanced organic chemistry. fourth ed. (1992), Wiley Interscience p. 443-444
18. Henbest H.B., and Wilson RAL. Aspects of stereochemistry. Part I. Stereospecificity in formation of epoxides from cyclic allylic alcohols. J Chem Soc (1957) 1958-1965
19. Glotter E., Greenfield S., and Lavie D. Studies on epoxides. Part II. Abnormal lithium aluminium hydride reduction of cis 3,4-epoxy-5-hydroxycholestanes. Tetrahedron Lett 8 (1967) 5261-5263
20. Hallsworth A.S., and Henbest H.B. Aspects of stereochemistry. Part VII. Metal reduction of vicinal epoxycyclohexanes. J Chem Soc (1957) 4604-4608
21. The energies of A-B ring conformations of the eight 4,5-epoxycholestane-3,6-diols (1-8) were minimised by using the tools in Chem3D Ultra 8.0 of ChemOffice 2004.
22. Li S., Pang J., Wilson W.K., and Schroepfer Jr. G.J. Sterol synthesis. Preparation and characterization of fluorinated and deuterated analogs of oxygenated derivatives of cholesterol. Chem Phys Lipids 99 (1999) 33-71
23. Urushibara K., and Mori Y. The formation of coprostane, 6β-coprostanol, and 3α,6β-coprostanediol by the catalytic reduction of epicholesterol β-oxide. Bull Chem Soc Jpn 31 (1958) 1068-1070
24. Plattner A., Fürst A., Müller A., and Keller W. Zur kenntnis der sesquiterpene und azulene. 108. Mitteilung. zur konstitution einiger azulen-carbonsäuren. Helv Chim Acta 37 (1954) 271-280
25. Anastasia M., Galli G.C., and Allevi P. Synthesis of 14β,17β(H)-cholest-5-en-3β-ol. J Org Chem 44 (1979) 4983-4986
26. Minato M., Yamamoto K., and Tsuji J. Osmium tetraoxide catalyzed vicinal hydroxylation of higher olefins by using hexacyanoferrate(III) ion as a cooxidant. J Org Chem 55 (1990) 766-768
27. Valisolalao J., Luu B., and Ourisson G. Steroides cytotoxiques de polyporus versicolor. Tetrahedron 39 (1983) 2779-2786
28. Coxon J.M., Hartshorn M.P., Lane G.A., Richards K.E., and Senanayake U.M. Acid catalysed rearrangements of some 5alpha-acetoxy steroids. Steroids 14 4 (1969) 441-447
29. Ramirez J.A., Centurion O.M.T., Gros E.G., and Galagovsky L.R. Synthesis and bioactivity evaluation of brassinosteroid analogs. Steroids 65 (2000) 329-337
30. Parish E.J., and Schroepfer Jr. G.J. Sterol synthesis. A simplified method for the synthesis of 32-oxygenated derivatives of 24,25-dihydrolanosterol. J Lipid Res 22 (1981) 859-888
31. Parish E.J., Luo C., and Boos T.L. A new chemical synthesis of 5α-cholest-8(14)-en-3β,5α-diol. Chem Phys Lipids 109 (2001) 113-115
32. Brown H.C., Ikegami S., and Kawakami Jr. J.H. Additions to bicyclic olefins. IV. Facile reduction of labile epoxides of bicyclic olefins by lithium in ethylenediamine. J Org Chem 35 (1970) 3243-3245
33. 7-Lanostene via 7α,8α-epoxides. Tetrahedron Lett 6 (1965) 2499-2504