Facile and highly diastereoselective formation of a novel pentacyclic scaffold by direct anodic oxidation of 2,4-dimethylphenol

被引：69
作者：
Malkowsky, IM
Rommel, CE
Wedeking, K
Fröhlich, R
Bergander, K
Nieger, M
Quaiser, C
Griesbach, U
Pütter, H
Waldvogel, SR
机构：
[1] Univ Munster, D-48149 Munster, Germany
[2] BASF Aktiengessch, D-67056 Ludwigshafen, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 01期
关键词：
electrochemistry; C-C coupling; oxidation; polycycles; phenols; spiro compounds;
D O I：
10.1002/ejoc.200500517
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Electrochemical oxidation of 2,4-dimethylphenol directly provides pentacyclic systems being generated by an oxidative trimerization. The major pentacyclic scaffold is exclusively formed as a single diastereoisomer and is easily isolated. Three further pentacyclic compounds which occur in minor quantities were also fully characterized including their solid-state structures. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
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页码：241 / 245
页数：5
相关论文
共 15 条
[1]   (ETA-6-BENZENE)(ETA-5-ETHYLTETRAMETHYLCYCLOPENTADIENYL)RHODIUM (III) HEXAFLUOROPHOSPHATE - A REAGENT FOR CATALYTIC PHENOL OXIDATIVE COUPLING [J].
BARRETT, AGM ;
ITOH, T ;
WALLACE, EM .
TETRAHEDRON LETTERS, 1993, 34 (14) :2233-2234
[2]   NEW CARBONYL COMPOUNDS FROM DEHYDROGENATION OF P-CRESOL [J].
CHEN, CL ;
CONNORS, WJ ;
SHINKER, WM .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :2966-&
[3]  
GRIMSHAW J, 2000, ELECTROCHEMICAL REAC, pCH6
[4]   THE OXIDATION OF MONOHYDRIC PHENOLS BY ALKALINE FERRICYANIDE [J].
HAYNES, CG ;
TURNER, AH ;
WATERS, WA .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (AUG) :2823-2831
[5]   The biosynthesis of plant alkaloids and nitrogenous microbial metabolites [J].
Herbert, RB .
NATURAL PRODUCT REPORTS, 2001, 18 (01) :50-65
[6]  
Hoshino O., 1998, The Alkaloids: Chemistry and Biology, P323
[7]   Aerobic catalytic oxidative coupling of 2-naphthols and phenols by VO(acac)2 [J].
Hwang, DR ;
Chen, CP ;
Uang, BJ .
CHEMICAL COMMUNICATIONS, 1999, (13) :1207-1208
[8]  
Lessene G., 2002, MODERN ARENE CHEM
[9]  
Martin S.F., 1988, The Alkaloids: Chemistry and Pharmacology, Elsevier, V30, P251
[10]   SYNTHESIS OF MORPHINANDIENONES, A DIHYDROPHENANTHRONE, AND PUMMERERS KETONES BY ANODIC COUPLING [J].
MILLER, LL ;
STEWART, RF ;
GILLESPIE, JP ;
RAMACHANDRAN, V ;
SO, YH ;
STERMITZ, FR .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1580-1586
12