DESIGN AND SYNTHESIS OF CONFORMATIONALLY CONSTRAINED BICYCLO[2.2.2]OCTANE-BASED UNUSUAL α-AMINO ACID DERIVATIVES VIA THE DIELS-ALDER REACTION

被引:6
作者
Kotha, Sambasivarao [1 ]
Meshram, Milind [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
Bicyclic alpha-Amino Acid Derivative; Anthracene Derivative; o-Quinodimethane; Diels-Alder Reaction; Glycine Equivalent; CARBOXYLIC-ACIDS; 9-SUBSTITUTED ANTHRACENES; REDUCTION; ALCOHOLS; METATHESIS;
D O I
10.3987/COM-14-S(K)26
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a simple synthetic approach to various conformationally constrained bicyclic alpha-amino acid derivatives using the Diels-Alder reaction as a key step. Moreover, we have investigated the reactivity pattern of various anthracene derivatives in relation to the Diels-Alder chemistry.
引用
收藏
页码:357 / 371
页数:15
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[1]   Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetrahydropyrazin-2-one structure [J].
Abellán, T ;
Mancheño, B ;
Nájera, C ;
Sansano, JM .
TETRAHEDRON, 2001, 57 (30) :6627-6640
[2]   Diels-Alder reactions of acyclic α-cyano α,β-alkenones: a new approach to highly substituted cyclohexene system [J].
Amancha, Prashanth K. ;
Lai, Yi-Chun ;
Chen, I-Chia ;
Liu, Hsing-Jang ;
Zhu, Jia-Liang .
TETRAHEDRON, 2010, 66 (04) :871-877
[3]   REDUCTION OF DMAD-ANTHRACENE ADDUCTS - SYNTHESIS AND CONFORMATIONS OF SUBSTITUTED CYCLODECADIENES [J].
ANANTANARAYAN, A ;
HART, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :991-996
[4]   Diels-Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes [J].
Atherton, JCC ;
Jones, S .
TETRAHEDRON, 2003, 59 (46) :9039-9057
[5]  
Balaram P., 1992, CURR OPIN STRUC BIOL, V2, P845, DOI [10.1016/0959-440X(92)90110-S, DOI 10.1016/0959-440X(92)90110-S]
[6]   Double diels-alder strategies to soluble 2,9- and 2,9,6,13-tetraethynylpentacenes, photolytic [4+4] cycloadditions, and pentacene crystal packing [J].
Benard, Christophe P. ;
Geng, Zhe ;
Heuft, Matthew A. ;
VanCrey, Kelly ;
Fallis, Alex G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7229-7236
[7]  
Blaskovich M. A., 2010, HDB SYNTHESIS AMINO
[8]  
Carruthers W., 1990, TETRAHEDRON ORGANIC, V8
[9]   Thermal and microwave assisted reactions of 2,5-disubstituted thienosultines with [60]fullerene: non-Kekule biradicals and self-sensitized oxygenation of the cycloadduct [J].
Chi, CC ;
Pai, IF ;
Chung, WS .
TETRAHEDRON, 2004, 60 (48) :10869-10876
[10]  
Dhar T.G.M., 2010, U.S. Patent, Patent No. [7,642,273, 7642273]