Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes

被引:31
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
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
收藏
页码:7961 / 7966
页数:6
相关论文
共 36 条
  • [1] Inhibitory activity of stilbenes from medicinal plants on the expression of cell adhesion molecules on THP1 cells
    Ahn, KS
    Kim, JH
    Oh, SR
    Ryu, SY
    Lee, HK
    [J]. 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
    Alonso, E
    Ramon, DJ
    Yus, M
    [J]. 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
    Azzena, U
    Idini, MV
    Pilo, L
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1309 - 1317
  • [6] REGIOSELECTIVE REDUCTIVE ELECTROPHILIC SUBSTITUTION OF DERIVATIVES OF 3,4,5-TRIMETHOXYBENZALDEHYDE
    AZZENA, U
    MELLONI, G
    PIRODDI, AM
    AZARA, E
    CONTINI, S
    FENUDE, E
    [J]. 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
    AZZENA, U
    MELLONI, G
    PISANO, L
    [J]. 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
    AZZENA, U
    DENURRA, T
    MELLONI, G
    PIRODDI, AM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5386 - 5390