OXYFUNCTIONALIZATION OF STEROIDS BY DIOXIRANES - SITE AND STEREOSELECTIVE C-14 AND C-17 HYDROXYLATION OF PREGNANE AND ANDROSTANE STEROIDS

被引:30
作者
BOVICELLI, P
LUPATTELLI, P
FIORINI, V
MINCIONE, E
机构
[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,CNR,CTR CHIM SOSTANZE ORGAN NAT,P A MORO 5,I-00185 ROME,ITALY
[2] UNIV TUSCIA,DABAC,I-01100 VITERBO,ITALY
关键词
D O I
10.1016/S0040-4039(00)61739-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dimethyldioxirane showed to be site and stereoselective in the C-H oxygen insertion of C-14 and C-17 positions of pregnane and androstane steroids. Fine steric control and evidence for the influence of the carbonyl group on the dioxirane reactivity are reported.
引用
收藏
页码:6103 / 6104
页数:2
相关论文
共 5 条
[1]  
BACH RD, IN PRESS
[2]   A HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE-C5 OXYFUNCTIONALIZATION OF COPROSTANE STEROIDS BY DIOXIRANES - AN IMPROVED ACCESS TO PROGESTOGEN AND ANDROGEN HORMONES [J].
BOVICELLI, P ;
GAMBACORTA, A ;
LUPATTELLI, P ;
MINCIONE, E .
TETRAHEDRON LETTERS, 1992, 33 (48) :7411-7412
[3]   OXIDATION OF NATURAL TARGETS BY DIOXIRANES - OXYFUNCTIONALIZATION OF STEROIDS [J].
BOVICELLI, P ;
LUPATTELLI, P ;
MINCIONE, E ;
PRENCIPE, T ;
CURCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2182-2184
[4]   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 [J].
BOVICELLI, P ;
LUPATTELLI, P ;
MINCIONE, E ;
PRENCIPE, T ;
CURCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5052-5054
[5]  
SLAMA K, 1974, INSECT HORMONES BIOA, P303