Galloyl-derived orthoquinones as reactive partners in nucleophilic additions and Diels-Alder dimerizations: A novel route to the dehydrodigalloyl linker unit of agrimoniin-type ellagitannins

被引：59

作者：

Feldman, KS ^{[1
]}

Quideau, S ^{[1
]}

Appel, HM ^{[1
]}

机构：

[1] PENN STATE UNIV, PESTICIDE RES LAB, UNIVERSITY PK, PA 16802 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 19期

关键词：

D O I：

10.1021/jo961043u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

引用

页码：6656 / 6665

页数：10

共 95 条

[31] PIPERIDINOCARBONYL RESIDUE AS A NEW IMINO PROTECTING GROUP FOR HISTIDINE [J].

JAGER, G ;

GEIGER, R ;

SIEDEL, W .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (10) :3537-&

[32] RHOIPTELEANIN-A AND RHOIPTELEANIN-E, DIMERIC ELLAGITANNINS FORMED BY INTERMOLECULAR C-C OXIDATIVE COUPLING FROM RHOIPTELEA-CHILIANTHA [J].

JIANG, ZH ;

TANAKA, T ;

KOUNO, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (14) :1467-1468

[33] PLANT POLYPHENOLS .6. EXPERIMENTS ON THE SYNTHESIS OF 3,3'-DI-O-METHYLELLAGIC AND 4,4'-DI-O-METHYLELLAGIC ACID [J].

JURD, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (17) :4606-4610

[34]

KAKIUCHI N, 1986, CHEM PHARM BULL, V34, P720

[35] INHIBITORY EFFECT OF TANNINS ON REVERSE-TRANSCRIPTASE FROM RNA TUMOR-VIRUS [J].

KAKIUCHI, N ;

HATTORI, M ;

NAMBA, T ;

NISHIZAWA, M ;

YAMAGISHI, T ;

OKUDA, T .

JOURNAL OF NATURAL PRODUCTS, 1985, 48 (04) :614-621

[36] ANTITUMOR AGENTS .129. TANNINS AND RELATED-COMPOUNDS AS SELECTIVE CYTOTOXIC AGENTS [J].

KASHIWADA, Y ;

NONAKA, G ;

NISHIOKA, I ;

CHANG, JJ ;

LEE, KH .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (08) :1033-1043

[37] TANNINS AS POTENT INHIBITORS OF DNA TOPOISOMERASE-II INVITRO [J].

KASHIWADA, Y ;

NONAKA, G ;

NISHIOKA, I ;

LEE, KJH ;

BORI, I ;

FUKUSHIMA, Y ;

BASTOW, KF ;

LEE, KH .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1993, 82 (05) :487-492

[38]

KELLY TR, 1978, TETRAHEDRON LETT, P4311

[39] NUCLEOPHILIC REACTIONS OF QUINONES [J].

KUTYREV, AA .

TETRAHEDRON, 1991, 47 (38) :8043-8065

[40] BORON SULFIDE AS A SOURCE OF ACYLOXYBORANE [J].

LALANCETTE, JM ;

BESSETTE, F ;

CLICHE, JM .

CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1966, 44 (13) :1577-+

← 1 2 3 4 5 6 7 8 9 10 →