TANDEM SILICA GEL-CATALYZED REARRANGEMENTS AND SUBSEQUENT BAEYER-VILLIGER REACTIONS OF ARTEMISININ DERIVATIVES

被引：18

作者：

YAGEN, B

PU, YM

YEH, HJC

ZIFFER, H

机构：

[1] NIDDKD,BETHESDA,MD 20892

[2] HEBREW UNIV JERUSALEM,SCH PHARM,DEPT NAT PROD,IL-91120 JERUSALEM,ISRAEL

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 07期

关键词：

D O I：

10.1039/p19940000843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel silica gel-catalysed reactions of dihydroartemisinin 1b to deoxyartemisinin 11 and 11 beta-hydroxy-11-epidihydroartemisinin 8 to compound 9 under mild conditions are described. The structures of the products were determined by mass spectrometry and 1D- and 2D-NMR spectroscopy. A mechanism for their formation is proposed.

引用

页码：843 / 846

页数：4

共 15 条

[1] ARTEETHER, A NEW ANTIMALARIAL DRUG - SYNTHESIS AND ANTIMALARIAL PROPERTIES
BROSSI, A
VENUGOPALAN, B
GERPE, LD
YEH, HJC
FLIPPENANDERSON, JL
BUCHS, P
LUO, XD
MILHOUS, W
PETERS, W
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (03) : 645 - 650
[2] ARTEMISININ (QINGHAOSU) - A NEW TYPE OF ANTIMALARIAL DRUG
BUTLER, AR
WU, YL
[J]. CHEMICAL SOCIETY REVIEWS, 1992, 21 (02) : 85 - 90
[3] DECOMPOSITION OF DIHYDROARTEMISITENE ON SILICA-GEL
ELFERALY, FS
AYALP, A
ALYAHYA, MA
MCPHAIL, DR
MCPHAIL, AT
[J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (04): : 920 - 925
[4] HUFFORD CD, 1990, PHARMACEUT RES, V7, P199
[5] QINGHAOSU (ARTEMISININ) - AN ANTIMALARIAL DRUG FROM CHINA
KLAYMAN, DL
[J]. SCIENCE, 1985, 228 (4703) : 1049 - 1055
[6] LIN AJ, 1991, MED CHEM RES, V1, P20
[7] THE CHEMISTRY, PHARMACOLOGY, AND CLINICAL-APPLICATIONS OF QINGHAOSU (ARTEMISININ) AND ITS DERIVATIVES
LUO, XD
SHEN, CC
[J]. MEDICINAL RESEARCH REVIEWS, 1987, 7 (01) : 29 - 52
[8] OGATA Y, 1972, J ORG CHEM, V27, P2853
[9] AN APPROACH TO THE SYNTHESIS OF NOVEL 11-HYDROXYARTEMISININ DERIVATIVES
PETROV, O
OGNYANOV, I
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (05) : 1037 - 1041
[10] A REGIOSPECIFICALLY O-18 LABELED 1,2,4-TRIOXANE - A SIMPLE CHEMICAL-MODEL SYSTEM TO PROBE THE MECHANISM(S) FOR THE ANTIMALARIAL ACTIVITY OF ARTEMISININ (QINGHAOSU)
POSNER, GH
OH, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8328 - 8329

← 1 2 →