Enantioselective synthesis of a benzofuranic neolignan by oxidative coupling

被引:42
作者
Bolzacchini, E
Brunow, G
Meinardi, S
Orlandi, M
Rindone, B
Rummakko, P
Setala, H
机构
[1] Univ Milan, Dept Environm Sci, I-20126 Milan, Italy
[2] Univ Helsinki, Dept Chem, FIN-00014 Helsinki, Finland
关键词
D O I
10.1016/S0040-4039(98)00473-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first stereoselective free radical coupling of a phenylpropenoidic phenolic compound is reported. The oxidation of a chiral ferulic acid amide to give dimeric benzofuranic neolignan is performed enzymatically using horseradish peroxidase as the catalyst. Enantiomeric excess in a biologically active compound with phenylcoumaran skeleton (beta-5 dimer) is thus obtained. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
引用
收藏
页码:3291 / 3294
页数:4
相关论文
共 16 条
  • [1] STUDIES ON DEGRADATION OF LIGNIN AND MODEL COMPOUNDS .1. CONFIGURATION OF DEHYDRODIISOEUGENOL
    AULINERDTMAN, G
    TOMITA, Y
    [J]. ACTA CHEMICA SCANDINAVICA, 1963, 17 (02): : 535 - &
  • [2] AYRES DC, 1990, LIGNANS CHEM BIOL CL, P278
  • [3] HYDROXYCINNAMIC ACID-DERIVED POLYMERS CONSTITUTE THE POLYAROMATIC DOMAIN OF SUBERIN
    BERNARDS, MA
    LOPEZ, ML
    ZAJICEK, J
    LEWIS, NG
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (13) : 7382 - 7386
  • [4] CELL-DIVISION PROMOTING ACTIVITY OF NATURALLY-OCCURRING DEHYDRODICONIFERYL GLUCOSIDES - DO CELL-WALL COMPONENTS CONTROL CELL-DIVISION
    BINNS, AN
    CHEN, RH
    WOOD, HN
    LYNN, DG
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (04) : 980 - 984
  • [5] REGIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF DIMERIC LIGNANS USING OXIDATIVE COUPLING
    CHIOCCARA, F
    POLI, S
    RINDONE, B
    PILATI, T
    BRUNOW, G
    PIETIKAINEN, P
    SETALA, H
    [J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (06): : 610 - 616
  • [6] Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center
    Davin, LB
    Wang, HB
    Crowell, AL
    Bedgar, DL
    Martin, DM
    Sarkanen, S
    Lewis, NG
    [J]. SCIENCE, 1997, 275 (5298) : 362 - 366
  • [7] ENZYME-MEDIATED H2O2 OXIDATION OF (E)-STILBENE-3,4-DIOL
    DONNELLY, DMX
    MURPHY, FG
    POLONSKI, J
    PRANGE, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12): : 2719 - 2722
  • [8] Fukuzumi T., 1978, MOKUZAI, V24, P664
  • [9] Higuchi T., 1985, Biosynthesis and biodegradation of wood components, DOI 10.1016/b978-0-12-347880-1.50011-8
  • [10] HIRAY N, 1994, BIOSCI BIOTECH BIOCH, V58, P1678