SITE-SELECTIVE HYDROXYLATION OF STEROIDS VIA OXOMETALLOPORPHINATES COVALENTLY LINKED TO RING-D - INTRODUCTION OF HYDROXYL-GROUPS INTO THE C(9) AND C(12) POSITION OF 5-ALPHA-ANDROSTANES

被引：32

作者：

STUK, TL ^{[1
]}

GRIECO, PA ^{[1
]}

MARSH, MM ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 09期

关键词：

D O I：

10.1021/jo00009a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of synthetic manganese(III) porphyrins attached to steroidal substrates at C(17) (cf. 2 and 3) gives rise to hydrogen atom abstraction at C(9) and/or C(12), thereby leading to hydroxyl incorporation at these sites. The use of more robust metalloporphyrins (cf. 9) results in substantial increases in the yields of hydroxylated 5-alpha-androstanes.

引用

页码：2957 / 2959

页数：3

共 21 条

[1] FLUORINATION AT SATURATED CARBON .2. DIRECT FLUORINATION OF STEROIDS
BARTON, DHR
HESSE, RH
MARKWELL, RE
PECHET, MM
ROZEN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) : 3036 - 3037
[2] THE SELECTIVE OXIDATION OF PROTECTED CHOLESTANOL DERIVATIVES USING THE GIF SYSTEM
BARTON, DHR
GOKTURK, AK
MORZYCKI, JW
MOTHERWELL, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (03): : 583 - 585
[3] MONOOXYGENASE-LIKE OXIDATION OF HYDROCARBONS BY H2O2 CATALYZED BY MANGANESE PORPHYRINS AND IMIDAZOLE - SELECTION OF THE BEST CATALYTIC-SYSTEM AND NATURE OF THE ACTIVE OXYGEN SPECIES
BATTIONI, P
RENAUD, JP
BARTOLI, JF
REINAARTILES, M
FORT, M
MANSUY, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) : 8462 - 8470
[4] BIOMIMETIC CONTROL OF CHEMICAL SELECTIVITY
BRESLOW, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (06) : 170 - 177
[5] REACTION OF IRON(III) PORPHYRINS AND IODOSOXYLENE - ACTIVE OXENE COMPLEX OF CYTOCHROME-P-450
CHANG, CK
KUO, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (12) : 3413 - 3415
[6] STUDIES IN STEROID GROUP .82. PREPARATION OF 9 MONOOXOANDROSTANES AND 8 DI-OXOANDROSTANES, 5 ALPHA-ESTRAN-17-ONE, AND 5 ALPHA-PREGNANE-2,20-DIONE
CLEGG, AS
MEAKINS, GD
KUMAR, V
THOMAS, VEM
DENNY, WA
JONES, ERH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (04): : 492 - &
[7] METALLOPORPHYRIN-CATALYZED OXIDATION OF SATURATED-HYDROCARBONS WITH SODIUM-CHLORITE
COLLMAN, JP
TANAKA, H
HEMBRE, RT
BRAUMAN, JI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3689 - 3690
[8] SHAPE SELECTIVE ALKANE HYDROXYLATION BY METALLOPORPHYRIN CATALYSTS
COOK, BR
REINERT, TJ
SUSLICK, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) : 7281 - 7286
[9] MODEL AND ENZYMATIC STUDIES WITH CYTOCHROME-P-450
DOLPHIN, D
JAMES, BR
LEUNG, T
[J]. INORGANICA CHIMICA ACTA-BIOINORGANIC CHEMISTRY, 1983, 79 (1-6): : 25 - 27
[10] REMOTE OXIDATION OF UNACTIVATED C-H BONDS IN STEROIDS VIA OXOMETALLOPORPHINATES
GRIECO, PA
STUK, TL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) : 7799 - 7801

← 1 2 3 →