Approach to the blues:: A highly flexible route to the azulenes

被引:46
作者
Carret, S [1 ]
Blanc, A [1 ]
Coquerel, Y [1 ]
Berthod, M [1 ]
Greene, AE [1 ]
Deprés, JP [1 ]
机构
[1] Univ Grenoble 1, Chim Rech LEDSS, F-38041 Grenoble, France
关键词
aromatic compounds; azulenes; cycloaddition; natural products; synthesis design;
D O I
10.1002/anie.200501276
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A palette of blues: Chlorobicyclo-[5.3.0] decatrienones are readily prepared from cycloheptatrienes by cycloaddition of dichloroketene, ring expansion with a diazoalkane, and dehydrochlorination in dimethylformamide. These compounds are used as intermediates in the regiocontrolled synthesis of a wide variety of natural and nonnatural azulenes (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5130 / 5133
页数:4
相关论文
共 38 条
[1]   AZULENIC RETINOIDS - NOVEL NONBENZENOID AROMATIC RETINOIDS WITH ANTICANCER ACTIVITY [J].
ASATO, AE ;
PENG, A ;
HOSSAIN, MZ ;
MIRZADEGAN, T ;
BERTRAM, JS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3137-3147
[2]   Stilbazulenyl nitrone (STAZN): A nitronyl-substituted hydrocarbon with the potency of classical phenolic chain-breaking antioxidants [J].
Becker, DA ;
Ley, JJ ;
Echegoyen, L ;
Alvarado, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4678-4684
[3]   THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].
BURGESS, EM ;
PENTON, HR ;
TAYLOR, EA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31
[4]  
Connolly JD, 1991, DICT TERPENOIDS, V2
[5]   New approach to bicyclo[5.3.0]decanes:: Stereoselective guaiane synthesis [J].
Coquerel, Y ;
Greene, AE ;
Deprés, JP .
ORGANIC LETTERS, 2003, 5 (23) :4453-4455
[6]   (1R,2s,3S,6R,9S)-5,5,10,10-tetra-chloro-2-methyltricyclo[7.2.0.03,6]undec-7-ene-4,11-dione [J].
Coquerel, Y ;
Blanc, A ;
Deprés, JP ;
Greene, AE ;
Averbuch-Pouchot, MT ;
Philouze, C ;
Durif, A .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2000, 56 (12) :1480-1481
[7]  
COQUEREL Y, 2001, THESIS U GRENOBLE
[8]   Donating strength of azulene in various azulen-1-yl-substituted cationic dyes: Application in nonlinear optics [J].
Cristian, L ;
Sasaki, I ;
Lacroix, PG ;
Donnadieu, B ;
Asselberghs, I ;
Clays, K ;
Razus, AC .
CHEMISTRY OF MATERIALS, 2004, 16 (18) :3543-3551
[9]   Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions [J].
Crombie, AL ;
Kane, JL ;
Shea, KM ;
Danheiser, RL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8652-8667
[10]  
Devon T.K., 1972, Handbook of Naturally Occurring Compounds: Terpenes, VVol. 2