The oxidation of 3-hydroxy-3-methyl-Δ4-steroids by chromium trioxide

被引：0
|
作者：
Uyanik, C
Hanson, JR [1 ]
Hitchcock, PB
机构：
[1] Univ Sussex, Dept Chem, Brighton BN1 9QJ, E Sussex, England
[2] Kocaeli Univ, Dept Chem, TR-41300 Izmit, Kocaeli, Turkey
来源：
JOURNAL OF CHEMICAL RESEARCH-S | 2003年 / 12期
关键词：
tertiary allylic alcohols; 3-hydroxy-3-methyl-Delta(4)-steroids; chromium trioxide; oxidation; epoxidation;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxidation of the allylic tertiary alcohols of 3-hydroxy-3-methyl-Delta(4)-steroids by chromium trioxide in sulfuric acid leads to C-C bond fission together with the formation of a 3-methylestra-1,3,5(10)-triene from a 19-nor steroid and a 3beta,4beta-epoxy-5beta-hydroxy compound from an androstane; the structure of the hydroxy-epoxide was established by X-ray crystallography.
引用
收藏
页码：795 / 797
页数：3
相关论文
共 50 条
  • [1] An unusual hydroboration of 3-hydroxy-3-methyl-Δ4-steroids
    Uyanik, C
    Hanson, JR
    Nisius, L
    Hitchcock, PB
    JOURNAL OF CHEMICAL RESEARCH, 2004, (07) : 471 - 473
  • [2] AROMATIC STEROIDS .3. CHROMIUM TRIOXIDE OXIDATION OF SOME 19-NORCHOLESTA-1,3,5(10)-TRIENES
    CAMBIE, RC
    CARLISLE, VF
    MANNING, TDR
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (09): : 1240 - &
  • [3] AROMATIC STEROIDS .4. CHROMIUM TRIOXIDE OXIDATION OF SOME OESTRA-1,3,5(10),9(11)-TETRAENES
    CAMBIE, RC
    CARLISLE, VF
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (12): : 1706 - &
  • [4] OXIDATION OF GLYCOSIDES .15. OXIDATION OF METHYL 4-OMICRON-METHYL-BETA-D-GLUCOPYRANOSIDE WITH CHROMIUM TRIOXIDE
    ASSARSSON, A
    THEANDER, O
    ACTA CHEMICA SCANDINAVICA, 1964, 18 (03): : 727 - &
  • [5] STEROIDS .132. OXIDATION OF 18-BENZOYLAMINOPROGESTERONE WITH CHROMIUM TRIOXIDE
    KASAL, A
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1970, 35 (12) : 3821 - &
  • [6] AROMATIC STEROIDS .2. CHROMIUM TRIOXIDE OXIDATION OF SOME OESTRA-1,3,5(10)-TRIENES
    CAMBIE, RC
    CARLISLE, VF
    LEQUESNE, CJ
    MANNING, TDR
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (09): : 1234 - &
  • [7] AROMATIC STEROIDS .5. CHROMIUM TRIOXIDE OXIDATION-PRODUCTS OF SOME AROMATIC STEROIDS
    CAMBIE, RC
    CARLISLE, VF
    DUVE, RN
    MANNING, TDR
    NEW ZEALAND JOURNAL OF SCIENCE, 1972, 15 (02): : 182 - 199
  • [8] OXIDATION OF METHYL 2-HYDROXY-3-METHYL-3-PHENYLINDOLIZINE-1-CARBOXYLATES AND METHYL-2-HYDROXY-3-PHENYLINDOLIZINE-1-CARBOXYLATES
    BOWERS, RJ
    BROWN, AG
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (10): : 1434 - &
  • [9] ALLYLIC OXIDATION OF METHYL TRANS-2-OCTADECENOATE BY CHROMIUM TRIOXIDE
    KHAN, M
    AHMAD, S
    AHMAD, MS
    OSMAN, SM
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (03): : 321 - 323
  • [10] Selective oxidation of α-hydroxy ketones to α-diketones with chromium trioxide supported on kieselghur reagent
    Lou, Ji-Dong
    Li, Li
    Vatanian, Negin
    Lu, Xiu Lian
    Yu, Xiaoping
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2008, 38 (04) : 373 - 375
12345