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Synthesis of Novel Fluoranthene-Based Conformationally Constrained alpha-Amino Acid Derivatives and Polycyclic Aromatics via the Diels-Alder Reaction

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Title Synthesis of Novel Fluoranthene-Based Conformationally Constrained alpha-Amino Acid Derivatives and Polycyclic Aromatics via the Diels-Alder Reaction
 
Creator KOTHA, S
MESHRAM, M
 
Subject amino acids
alkylation
bioorganic chemistry
fusedring systems
Diels-Alder reaction
ORGANIC ELECTRONICS
COUPLING REACTION
CYCLOADDITION
ACENES
 
Description Conformationally constrained cyclic alpha-amino acid moieties have been fused to the fluoranthene system. Aminoindanecarboxylic acid (Aic) and 1,2,3,4-tetrahydroisoquinolinecarboxylic acid (Tic) derivatives were synthesized by an alkylation sequence, whereas a aminotetralincarboxylic acid (Atc) derivative was assembled using the Diels-Alder reaction as a key step. These a-amino acid derivatives are considered as constrained analogues of phenylalanine (Phe) and play an important role in the design and synthesis of bioactive peptides and some fluorescence chemosensor molecules. Moreover, this strategy has been extended to polycyclic aromatics via the Diels-Alder reaction and subsequent aromatization with DDQ.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2014-12-28T11:56:01Z
2014-12-28T11:56:01Z
2014
 
Type Article
 
Identifier SYNTHESIS-STUTTGART, 46(11)1525-1531
0039-7881
1437-210X
http://dx.doi.org/10.1055/s-0033-1341042
http://dspace.library.iitb.ac.in/jspui/handle/100/16414
 
Language English