Synthesis of novel quinone-amino acid hybrids via cross-enyne metathesis and Diels-Alder reaction as key steps

被引:40
作者
Kotha, Sambasivarao [1 ]
Mandal, Kalyaneswar [1 ]
Banerjee, Shaibal [1 ]
Mobin, Shaikh M. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
quinone-amino acid hybrids; cross-enyne metathesis; cycloaddition; fullerenes;
D O I
10.1002/ejoc.200600970
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A "Building Block Approach" for the synthesis of various quinone-amino acid hybrids through ethylene cross-enyne metathesis and Diels-Alder reaction as key steps is described. A library of comformationally constrained quinone-based phenylalanine derivatives and dicarba analogs of cystine have been generated starting from a common precursor using Grubbs' catalysts. This methodology has also been extended for the synthesis of fullerene-based dicarba analogs of cystine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
引用
收藏
页码:1244 / 1255
页数:12
相关论文
共 115 条
[1]   Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis [J].
Aguilera, B ;
Wolf, LB ;
Nieczypor, P ;
Rutjes, FPJT ;
Overkleeft, HS ;
van Hest, JCM ;
Schoemaker, HE ;
Wang, B ;
Mol, JC ;
Fürstner, A ;
Overhand, M ;
van der Marel, GA ;
van Boom, JH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3584-3589
[2]   Site-specific incorporation of a redox-active amino acid into proteins [J].
Alfonta, L ;
Zhang, ZW ;
Uryu, S ;
Loo, JA ;
Schultz, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14662-14663
[3]   New quinone-amino acid conjugates linked via a vinylic spacer [J].
Alnabari, M ;
Bittner, S .
AMINO ACIDS, 2001, 20 (04) :381-387
[4]   The Nicholas approach to natural product hybrids [J].
Alvaro, Elsa ;
de la Torre, Maria C. ;
Sierra, Miguel A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (24) :6403-6411
[5]   SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES OF C-60 FROM 1,9-(4-HYDROXYCYCLOHEXANO)-BUCKMINSTERFULLERENE [J].
AN, YZ ;
ANDERSON, JL ;
RUBIN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4799-4801
[6]  
[Anonymous], MODERN SYNTHETIC MET
[7]  
[Anonymous], 1995, P 3 INT C DOC AN REC
[8]  
[Anonymous], 1978, Top. Stereochem
[9]  
Arndt S, 2001, CHEM-EUR J, V7, P993, DOI 10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO
[10]  
2-S