1ST-SYNTHESIS AND STRUCTURAL DETERMINATION OF BLEPHARIN AND 1'-EPIBLEPHARIN

被引:25
作者
TIETZE, LF
BELLER, M
TERFORT, A
DOLLE, A
机构
来源
SYNTHESIS-STUTTGART | 1991年 / 12期
关键词
D O I
10.1055/s-1991-28401
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of the natural acetal-beta-D-glucoside blepharin (1) and its C-2' epimer 9 by treatment of 2-bromo-H-2-1,4-benzoxazin-3(4H)-one (5) with 2.3,4,6-tetra-O-acetyl-beta-D-glucopyranose (6) is described. The relative and absolute configuration of 1 was determined by H-1-NMR and X-ray analysis.
引用
收藏
页码:1118 / 1120
页数:3
相关论文
共 12 条
[1]  
[Anonymous], 1983, ANGEW CHEM, V95, P902
[2]  
CHATTERJEE A, 1969, CHEM IND-LONDON, P328
[3]   1,4-BENZOXAZINE DERIVATIVES IN PLANTS - SEPHADEX FRACTIONATION AND IDENTIFICATION OF A NEW GLUCOSIDE [J].
HOFMAN, J ;
HOFMANOVA, O .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1969, 8 (01) :109-+
[4]   THE SYNTHESIS OF PRECURSOR-II OF BENZOXAZOLINONE FORMED IN RYE PLANTS, AND THE ENZYMIC HYDROLYSIS OF PRECURSOR-I, THE GLUCOSIDE [J].
HONKANEN, E ;
VIRTANEN, AI .
ACTA CHEMICA SCANDINAVICA, 1960, 14 (02) :504-507
[5]   SYNTHESIS OF SOME 1,4-BENZOXAZINE DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY [J].
HONKANEN, E ;
VIRTANEN, AI .
ACTA CHEMICA SCANDINAVICA, 1960, 14 (05) :1214-1217
[6]   BENZOXAZINONES FROM COIX-LACHRYMA-JOBI VAR MA-YUEN [J].
NAGAO, T ;
OTSUKA, H ;
KOHDA, H ;
SATO, T ;
YAMASAKI, K .
PHYTOCHEMISTRY, 1985, 24 (12) :2959-2962
[7]   ANTI-INFLAMMATORY ACTIVITY OF BENZOXAZINOIDS FROM ROOTS OF COIX-LACHRYMA-JOBI VAR MA-YUEN [J].
OTSUKA, H ;
HIRAI, Y ;
NAGAO, T ;
YAMASAKI, K .
JOURNAL OF NATURAL PRODUCTS, 1988, 51 (01) :74-79
[8]   EUROPEAN CORN-BORER - (LEPIDOPTERA-PYRALIDAE) NONPREFERENCE MECHANISM OF LEAF FEEDING RESISTANCE AND ITS RELATIONSHIP TO 1,4-BENZOXAZIN-3-ONE CONCENTRATION IN DENT CORN TISSUE [J].
ROBINSON, JF ;
KLUN, JA ;
BRINDLEY, TA .
JOURNAL OF ECONOMIC ENTOMOLOGY, 1978, 71 (03) :461-465
[9]  
SHELDRICK GM, 1986, SHELXTL USER MANUAL
[10]   IRIDOIDS .19. STEREOSELECTIVE SYNTHESIS OF IRIDOID GLYCOSIDES [J].
TIETZE, LF ;
FISCHER, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (11) :888-888