ON THE SYNTHESIS OF HYPERICIN BY OXIDATIVE TRIMETHYL-EMODIN ANTHRONE AND EMODIN ANTHRONE DIMERIZATION - ISOHYPERICIN

被引：55

作者：

FALK, H

SCHOPPEL, G

机构：

[1] Institut für Chemie, Johannes-Kepler-Universität Linz, Linz

来源：

MONATSHEFTE FUR CHEMIE | 1992年 / 123卷 / 10期

关键词：

TRIMETHYLEMODIN ANTHRONE; EMODIN ANTHRONE; HYPERICIN; ISOHYPERICIN; SPECTROSCOPIC PROPERTIES; PKA-VALUES; SYNTHESIS;

D O I：

10.1007/BF00811548

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonation pK(a) and pK(a)* values.

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页码：931 / 938

页数：8

相关论文

共 13 条

[1] DYNAMIC STEREOCHEMISTRY IN OVERCROWDED ETHYLENES - CONFORMATIONAL BEHAVIOR OF BIANTHRONES [J].

AGRANAT, I ;

TAPUHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) :1941-1948

[2] CHEMISTRY OF COCCOIDEA .2. CONDENSED POLYCYCLIC PIGMENTS FROM 2 AUSTRALIAN PSEUDOCOCCIDS (HEMIPTERA) [J].

BANKS, HJ ;

CAMERON, DW ;

RAVERTY, WD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (07) :1509-1521

[3] TOTALSYNTHESE DES HYPERICINS [J].

BROCKMANN, H ;

KLUGE, F ;

MUXFELDT, H .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10) :2302-2318

[4] SYNTHESE DES PROTO-HYPERICINS UND HYPERICINS AUS EMODIN-ANTHRON-(9) [J].

BROCKMANN, H ;

EGGERS, H .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (03) :547-553

[5] OXIDATION OF EMODIN ANTHRONE AND STEREOCHEMISTRY OF EMODIN BIANTHRONE [J].

CAMERON, DW ;

EDMONDS, JS ;

RAVERTY, WD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (07) :1535-1548

[6] PSEUDOHYPERICIN AND OTHER PHENANTHROPERYLENE QUINONES [J].

CAMERON, DW ;

RAVERTY, WD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (07) :1523-1533

[7] DEPROTONATION AND PROTONATION OF HYDROXYPHENANTHROPERYLENES [J].

FALK, H ;

MEYER, J ;

OBERREITER, M .

MONATSHEFTE FUR CHEMIE, 1992, 123 (03) :277-284

[8] ON THE NATURE OF SOLUBLE HYPERICIN IN HYPERICUM SPECIES [J].

FALK, H ;

SCHMITZBERGER, W .

MONATSHEFTE FUR CHEMIE, 1992, 123 (8-9) :731-739

[9] A SYNTHESIS OF EMODIN ANTHRONE [J].

FALK, H ;

SCHOPPEL, G .

MONATSHEFTE FUR CHEMIE, 1991, 122 (8-9) :739-744

[10] RECHERCHES SUR LEO DROGUES A PRINCIPES ANTHRAQUINONIQUES .16. DETERMINATION DE LA STRUCTURE DES DERIVES ANTHRACENIQUES REDUITS DE LECORCE DE RHAMNUS PURSHIANA DC [J].

KINGET, R .

PLANTA MEDICA, 1967, 15 (03) :233-&