Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide

被引：6
作者：
Grainger, Wendell S. [1 ]
Parish, Edward J. [1 ]
机构：
[1] Auburn Univ, Coll Sci & Math, Dept Chem & Biochem, Auburn, AL 36849 USA
来源：
STEROIDS | 2015年 / 101卷
关键词：
Oxidation; 7-Ketocholesterol; Vanadyl acetylacetonate; tert-Butyl hydroperoxide; ASYMMETRIC EPOXIDATION; SPECTRAL PROPERTIES; MOLYBDENUM; 7-DEHYDROCHOLESTEROL; OXYSTEROLS; CATALYST; ALCOHOLS; ACETATE; STEROLS;
D O I：
10.1016/j.steroids.2015.06.005
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Readily available vanadyl acetylacetonate was found to oxidize the allylic sites of Delta(5) steroidal alcohols without protection of hydroxyl groups. Cholesterol, dehydroepiandrosterone, cholesterol benzoate, cholesterol acetate, pregnenolone, and 5-pregnen-3,20-diene were oxidized to 7-keto products using vanadyl acetylacetonate in one pot reactions at room temperature in the presence of oxygen and water. (C) 2015 Elsevier Inc. All rights reserved.
引用
收藏
页码：103 / 109
页数：7
相关论文
共 29 条
  • [1] Functionalization of oxo-vanadium(IV) acetylacetonate over modified MCM-41: an efficient reusable catalyst for epoxidation reaction
    Bhunia, Susmita
    Koner, Subratanath
    [J]. JOURNAL OF POROUS MATERIALS, 2011, 18 (04) : 399 - 407
  • [2] Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis
    Carvalho, Joao F. S.
    Manuel Cruz Silva, M.
    Moreira, Joao N.
    Simoes, Sergio
    Luisa Sa e Melo, M.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (21) : 7632 - 7638
  • [3] MECHANISM OF MOLYBDENUM AND VANADIUM CATALYZED EPOXIDATION OF OLEFINS BY ALKYL HYDROPEROXIDES
    CHONG, AO
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (09) : 1587 - 1590
  • [4] Cormier KW, 2012, CHEN CHUO CHEM SCI, V3, P2240
  • [5] Oxovanadium complexes in catalytic oxidations
    da Silva, Jose A. L.
    Frausto da Silva, Joao J. R.
    Pombeiro, Armando J. L.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (19-20) : 2232 - 2248
  • [6] ALLYLIC OXIDATION OF OLEFINS WITH CHROMIUM TRIOXIDE-PYRIDINE COMPLEX
    DAUBEN, WG
    LORBER, M
    FULLERTON, DS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (11) : 3587 - +
  • [7] Importance of cholesterol and oxysterols metabolism in the pharmacology of tamoxifen and other AEBS ligands
    de Medina, Philippe
    Paillasse, Michael R.
    Segala, Gregory
    Khallouki, Farid
    Brillouet, Severine
    Dalenc, Florence
    Courbon, Frederic
    Record, Michel
    Poirot, Marc
    Silvente-Poirot, Sandrine
    [J]. CHEMISTRY AND PHYSICS OF LIPIDS, 2011, 164 (06) : 432 - 437
  • [8] Synthesis of 7-dehydrocholesterol through a palladium catalyzed selective homoannular conjugated diene formation
    Dugas, Diane
    Brunel, Jean Michel
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) : 119 - 122
  • [9] Oxidative metabolism of dehydroepiandrosterone (DHEA) and biologically active oxygenated metabolites of DHEA and epiandrosterone (EpiA) - Recent reports
    El Kihel, Laila
    [J]. STEROIDS, 2012, 77 (1-2) : 10 - 26
  • [10] KIMURA M, 1981, CHEM PHARM BULL, V29, P35
123