Chain extension of aldonolactones by samarium iodide mediated Dreiding-Schmidt reactions and samarium assisted Imamoto reactions

被引:15
作者
Csuk, R [1 ]
Horing, U [1 ]
Schaade, M [1 ]
机构
[1] UNIV HEIDELBERG,PHARM CHEM INST,D-69120 HEIDELBERG,GERMANY
关键词
D O I
10.1016/0040-4020(96)00508-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unprecedented SmI2 mediated Dreiding-Schmidt reactions were used for chain extension reactions of aldonolactones with alkyl 2-bromomethyl acrylates or 2-bromomethyl-acrylonitrile, respectively. The reaction of aldonolactones with diiodomethane in the presence of samarium powder resulted in the formation of polyhydroxyalkyl substituted cyclopropanols. Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:9759 / 9776
页数:18
相关论文
共 61 条
[21]   THE MECHANISM OF ACTION OF VITAMIN-B12 [J].
DOWD, P ;
SHAPIRO, M ;
KANG, J .
TETRAHEDRON, 1984, 40 (16) :3069-3086
[22]   THE REFORMATSKY REACTION OF ETHYL ALPHA-(BROMOMETHYL)ACRYLATE WITH ACYL CHLORIDES AND NITRILES [J].
ELALAMI, N ;
BELAUD, C ;
VILLIERAS, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 319 (03) :303-309
[23]  
FUJI K, 1975, SYNTHESIS-STUTTGART, P276
[24]  
GAREGG PJ, 1993, ACS S SERIES, V519
[25]  
GRIECO PA, 1974, TETRAHEDRON LETT, P3467
[26]   PRACTICAL SYNTHESIS OF "ALPHA-METHYLENE-GAMMA-BUTYROLACTONE [J].
GRIECO, PA ;
POGONOWS.CS .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1958-1959
[27]   HELENANOLIDES - STEREOCONTROLLED TOTAL SYNTHESIS OF DL-BIGELOVIN, DL-MEXICANIN-I, AND DL-LINIFOLIN-A [J].
GRIECO, PA ;
OHFUNE, Y ;
MAJETICH, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :360-366
[28]   PREPARATIVE AND EXPLORATORY CARBOHYDRATE CHEMISTRY - PROCEDURES FOR DIRECT REPLACEMENT OF PRIMARY HYDROXYL GROUPS IN CARBOHYDRATES BY HALOGEN [J].
HANESSIAN, S ;
PONPIPOM, MM ;
LAVALLEE, P .
CARBOHYDRATE RESEARCH, 1972, 24 (01) :45-+
[29]  
HANESSIAN S, 1994, SYNLETT, P865
[30]  
Hanessian S., 1983, Total Synthesis of Natural Products: The Chiron Approach