OXIDATION OF NATURAL TARGETS BY DIOXIRANES .2. DIRECT HYDROXYLATION AT THE SIDE-CHAIN C-25 OF CHOLESTANE DERIVATIVES AND OF VITAMIN-D3 WINDAUS-GRUNDMANN KETONE

被引：77
作者：
BOVICELLI, P
LUPATTELLI, P
MINCIONE, E
PRENCIPE, T
CURCI, R
机构：
[1] UNIV BARI,DEPT CHEM,CTR MISO,CNR,V AMENDOLA 173,I-70126 BARI,ITALY
[2] UNIV ROME LA SAPIENZA,DEPT CHEM,CTR CSON,CNR,I-00185 ROME,ITALY
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期
关键词：
D O I：
10.1021/jo00045a004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue.
引用
收藏
页码：5052 / 5054
页数：3
相关论文
共 47 条
[11]   O-17 AND C-13 IDENTIFICATION OF THE DIMETHYLDIOXIRANE INTERMEDIATE ARISING IN THE REACTION OF POTASSIUM CARBONATE WITH ACETONE [J].
CASSIDEI, L ;
FIORENTINO, M ;
MELLO, R ;
SCIACOVELLI, O ;
CURCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :699-700
[12]   STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN THE EPOXIDATION OF SOME ALLYLIC ALCOHOLS BY THE DIOXIRANE INTERMEDIATE GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH ACETONE [J].
CICALA, G ;
CURCI, R ;
FIORENTINO, M ;
LARICCHIUTA, O .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2670-2673
[13]   HYDROXYLATION WITH OZONE ON SILICA-GEL - SYNTHESIS OF 1 ALPHA,25-DIHYDROXYVITAMIN-D3 [J].
COHEN, Z ;
KEINAN, E ;
MAZUR, Y ;
ULMAN, A .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (15) :2651-2652
[14]   DRY OZONATION OF STEROIDS - C-25 FUNCTIONALIZATION OF CHOLESTANE DERIVATIVES [J].
COHEN, Z ;
MAZUR, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2318-2320
[15]   EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].
CURCI, R ;
FIORENTINO, M ;
TROISI, L ;
EDWARDS, JO ;
PATER, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760
[16]  
CURCI R, 1990, ADV OXYGENATED PROCE, V2, pCH1
[17]  
DATCHEVA V K, 1989, Steroids, V54, P271, DOI 10.1016/0039-128X(89)90002-0
[18]   CHOLESTEROL AND COMPANIONS .7. STEROID DIBROMIDES [J].
FIESER, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (21) :5421-5422
[19]  
FIESER LF, 1957, J ORG CHEM, V22, P1380
[20]   A STEREOSPECIFIC ROUTE TO 2-DEOXY-BETA-GLYCOSIDES [J].
GERVAY, J ;
DANISHEFSKY, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5448-5451
12345