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Synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches

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Title Synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches
 
Creator KOTHA, S
SREENIVASACHARY, N
 
Subject alpha-amino-acids
ring-closing metathesis
solid-phase synthesis
asymmetric-synthesis
organic-synthesis
alpha,beta-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
nickel(0)-catalyzed -cocyclization
isoquinoline derivatives
constrained analogs
olefin metathesis
amino acids
combinatorial chemistry
drug design
metathesis
peptides
peptidomimetics
 
Description A new and general synthetic methodology for the preparation of functionalized 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives by a cycloaddition strategy is described. The synthesis of various enyne building blocks 12, 13, 21, and 22 containing an alpha -amino acid moiety using Schiff base 8 as a glycine equivalent has been achieved under mild reaction conditions. These building blocks have been utilized in the synthesis of inner-outer ring dienes 23 and 24 and exocyclic dienes 26 and 29, the key steps being an enyne metathesis reaction and cycloisomerization. Various topographically constrained Tic derivatives have been synthesized using dienes containing an alpha -amino acid moiety through Diels-Alder reactions. For the first time, [2+2+2] cyclotrimerization, as promoted by Wilkinson's and Vollhardt's catalysts, has been used for the synthesis of various highly functionalized Tic derivatives.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2011-09-01T21:25:49Z
2011-12-26T12:59:48Z
2011-12-27T05:52:41Z
2011-09-01T21:25:49Z
2011-12-26T12:59:48Z
2011-12-27T05:52:41Z
2001
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (17), 3375-3383
1434-193X
http://dspace.library.iitb.ac.in/xmlui/handle/10054/12872
http://hdl.handle.net/10054/12872
 
Language en