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Diversity-Oriented Approaches to Unusual alpha-Amino Acids and Peptides: Step Economy, Atom Economy, Redox Economy, and Beyond

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Title Diversity-Oriented Approaches to Unusual alpha-Amino Acids and Peptides: Step Economy, Atom Economy, Redox Economy, and Beyond
 
Creator KOTHA, S
GOYAL, D
CHAVAN, AS
 
Subject CROSS-COUPLING REACTION
DIELS-ALDER REACTION
RING-CLOSING METATHESIS
CONSTRAINED PHENYLALANINE DERIVATIVES
OPTICALLY-ACTIVE BENZOCYCLOBUTENE
2+2+2 CYCLOADDITION STRATEGY
PICTET-SPENGLER REACTION
BUILDING-BLOCK APPROACH
N-ACYLIMINIUM IONS
ENYNE METATHESIS
 
Description Here we describe several useful strategies to a variety of unusual a-amino acid derivatives and peptides based on "building block" approach. These building blocks are suitable for modification at an amino acid as well as at a peptide level. Moreover, these methods have embedded several points for diversification and are capable of producing a library of modified amino acids and peptides. We have employed highly atom-economic processes such as the Diels-Alder reaction, [2 + 2 + 2] cycloaddition, Suzuki-Miyaura cross-coupling, and olefin metathesis as key steps to assemble various unnatural amino acid derivatives and peptides. In some instances, we have used rongalite to generate Diels-Alder precursors.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-16T06:07:39Z
2014-10-16T06:07:39Z
2013
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 78(24)12288-12313
http://dx.doi.org/10.1021/jo4020722
http://dspace.library.iitb.ac.in/jspui/handle/100/15415
 
Language en