Enantioselective synthesis of a benzofuranic neolignan by oxidative coupling

被引：41

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期

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 [J].

AULINERDTMAN, G ;

TOMITA, Y .

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 [J].

BERNARDS, MA ;

LOPEZ, ML ;

ZAJICEK, J ;

LEWIS, NG .

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 [J].

BINNS, AN ;

CHEN, RH ;

WOOD, HN ;

LYNN, DG .

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 [J].

CHIOCCARA, F ;

POLI, S ;

RINDONE, B ;

PILATI, T ;

BRUNOW, G ;

PIETIKAINEN, P ;

SETALA, H .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (06) :610-616

[6] Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center [J].

Davin, LB ;

Wang, HB ;

Crowell, AL ;

Bedgar, DL ;

Martin, DM ;

Sarkanen, S ;

Lewis, NG .

SCIENCE, 1997, 275 (5298) :362-366

[7] ENZYME-MEDIATED H2O2 OXIDATION OF (E)-STILBENE-3,4-DIOL [J].

DONNELLY, DMX ;

MURPHY, FG ;

POLONSKI, J ;

PRANGE, T .

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