Oxidative transformation of the natural lignan hydroxymatairesinol with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone

被引：34

作者：

Eklund, PC ^{[1
]}

Sjöholm, RE ^{[1
]}

机构：

[1] Abo Akad Univ, Dept Organ Chem, Proc Chem Grp, Turku 20500, Finland

来源：

TETRAHEDRON | 2003年 / 59卷 / 25期

关键词：

hydroxymatairesinol; lignan; oxidative transformation; DDQ; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; benzylic hydroxylation; dehydrogenation;

D O I：

10.1016/S0040-4020(03)00683-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative transformation of the two isomers of the natural lignan hydroxymatairesinol from Norway Spruce (Picea abies) by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), has been studied. Significant differences in the outcome of the reactions were observed when the pure isomers of hydroxymatairesinol were reacted with DDQ under the same conditions. The different stereoelectronic effects in the two isomers as well as their conformational structures seem to determine the site of reaction, which results in different reaction products. Several products were identified by GC-MS and NMR spectroscopy. Oxomatairesinol was obtained in a yield of 25%. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4515 / 4523

页数：9

共 34 条

[1]

ADLERCREUTZ H, 1981, MED BIOL, V59, P259

[2] NOVEL HYDROXY LIGNANS FROM HEARTWOOD OF GMELINA-ARBOREA [J].

ANJANEYULU, ASR ;

RAO, AM ;

RAO, VK ;

ROW, LR ;

PELTER, A ;

WARD, RW .

TETRAHEDRON, 1977, 33 (01) :133-143

[3]

[Anonymous], 1990, LIGNANS CHEM BBIOLOG

[4] QUINONE DEHYDROGENATION - OXIDATION OF BENZYLIC ALCOHOLS WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE [J].

BECKER, HD ;

BJORK, A ;

ADLER, E .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1596-1600

[5] LIGNANES .15. 1ST TOTAL SYNTHESIS OF NATURAL (-)-ALPHA-CONIDENDRIN [J].

BOISSIN, P ;

DHAL, R ;

BROWN, E .

TETRAHEDRON, 1992, 48 (04) :687-694

[6] APPLICATIONS OF HIGH POTENTIAL QUINONES .9. STEREOELECTRONIC EFFECT IN RATES OF QUINONE DEHYDROGENATION OF BENZOCYCLOALKENOLS [J].

BROWN, DR ;

TURNER, AB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (12) :1307-1309

[7] Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries [J].

Charlton, JL ;

Chee, GL .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (08) :1076-1083

[8]

COLE JC, 1978, CHEM LIGNANS

[9]

EKLUND P, 2002, J CHEM SOC P1, V19, P1906

[10] ANALYSIS OF LIGNANS IN NORWAY SPRUCE BY COMBINED GAS-CHROMATOGRAPHY - MASS-SPECTROMETRY [J].

EKMAN, R .

HOLZFORSCHUNG, 1976, 30 (03) :79-85

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