The reaction of Grignard reagents with steroidal 2-spiro-1,3-dioxolanes

被引:0
作者
Caballero, GM [1 ]
Gros, EG [1 ]
机构
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
来源
ANALES DE LA ASOCIACION QUIMICA ARGENTINA | 1997年 / 85卷 / 3-4期
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3-Cycloethyleneacetal- and 17-cycloethyleneacetal-androstene derivatives react with a great molar excess (22:1) of methylmagnesium iodide to afford the corresponding 3-methyl-3-(hydroxy-ethoxy) and 17-methyl-17-(hydroxy-ethoxy) compounds respectively as single C-3 or C-17 epimers, The stereoselectivity of the title reaction is discussed in terms of the probable reaction mechanisms.
引用
收藏
页码:111 / 116
页数:6
相关论文
共 12 条
[1]   MECHANISM OF ACETAL CLEAVAGE WITH METHYLMAGNESIUM IODIDE [J].
ABELL, AD ;
MASSYWESTROPP, RA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (07) :1031-1036
[2]  
[Anonymous], 1989, NUCL OVERHAUSER EFFE, DOI DOI 10.1002/MRC.1260280819
[3]   CLEAVAGE OF CARBON-OXYGEN SINGLE BONDS IN REACTION OF ARYL ETHYL ACETALS WITH ETHYLMAGNESIUM BROMIDE IN DIETHYL-ETHER - KINETIC STUDY [J].
BELTRAME, P ;
GELLI, G ;
LOI, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (09) :1001-1003
[4]  
BURKERT U, 1982, ACS MONOGRAPH, V177
[5]   SYNTHESIS OF [20,21(C-13)2]-PROGESTERONE [J].
CABALLERO, GM ;
GROS, EG .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1991, 29 (07) :805-812
[6]   CLEAVAGE OF ACETALS PROMOTED BY COPPER (II) SULFATE ADSORBED ON SILICA-GEL [J].
CABALLERO, GM ;
GROS, EG .
SYNTHETIC COMMUNICATIONS, 1995, 25 (03) :395-404
[7]  
HAMPEL B, 1966, TETRAHEDRON, V22, P1601
[8]  
HAURANEK RE, 1966, J MED CHEM, V9, P326
[9]  
KAY AI, 1951, J AM CHEM SOC, V73, P4893
[10]  
March J., 1992, ADV ORG CHEM