Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes

被引：32

作者：

Azzena, U ^{[1
]}

Dettori, G ^{[1
]}

Idini, MV ^{[1
]}

Pisano, L ^{[1
]}

Sechi, G ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 40期

关键词：

reduction; electron transfer; regioselectivity; stilbenes;

D O I：

10.1016/j.tet.2003.08.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective removal of the 4-methoxy group of 3,4,5-trimethoxystilbenes was performed under electron transfer conditions from Na metal in THF. Careful control of reaction conditions and quenching procedure allowed the synthesis of either (E)-3,5-dimethoxystilbenes or 3,5-dimethoxybibenzyls. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7961 / 7966

页数：6

共 36 条

[1] Inhibitory activity of stilbenes from medicinal plants on the expression of cell adhesion molecules on THP1 cells [J].

Ahn, KS ;

Kim, JH ;

Oh, SR ;

Ryu, SY ;

Lee, HK .

PLANTA MEDICA, 2000, 66 (07) :641-644

[2]

ALI MA, 1992, CHEM PHARM BULL, V40, P1130, DOI 10.1248/cpb.40.1130

[3] Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules [J].

Alonso, E ;

Ramon, DJ ;

Yus, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :417-421

[4]

AZZENA U, 1990, SYNTHESIS-STUTTGART, P313

[5] Synthesis of antibiotic stilbenes by reductive metalation of 3,4,5-trimethoxybenzaldehyde dimethyl acetal [J].

Azzena, U ;

Idini, MV ;

Pilo, L .

SYNTHETIC COMMUNICATIONS, 2003, 33 (08) :1309-1317

[6] REGIOSELECTIVE REDUCTIVE ELECTROPHILIC SUBSTITUTION OF DERIVATIVES OF 3,4,5-TRIMETHOXYBENZALDEHYDE [J].

AZZENA, U ;

MELLONI, G ;

PIRODDI, AM ;

AZARA, E ;

CONTINI, S ;

FENUDE, E .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3101-3106

[7] REGIOSELECTIVITY IN THE REDUCTIVE CLEAVAGE OF PYROGALLOL DERIVATIVES - REDUCTIVE ELECTROPHILIC SUBSTITUTION OF ACETALS OF 2,3-DIMETHOXYPHENOL [J].

AZZENA, U ;

MELLONI, G ;

PISANO, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (03) :261-266

[8]

Azzena U, 1997, TREND ORGAN CHEM, V6, P55

[9]

AZZENA U, 1989, SYNTHESIS-STUTTGART, P28

[10] REGIOSELECTIVE REDUCTIVE ELECTROPHILIC SUBSTITUTION OF 1,2,3-TRIMETHOXYBENZENE AND ITS 5-ALKYL-SUBSTITUTED HOMOLOGS [J].

AZZENA, U ;

DENURRA, T ;

MELLONI, G ;

PIRODDI, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5386-5390

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