Synthesis of Diketopiperazine Scaffolds with Tailored N‐ and α‐Chains by Selective Modification of Customizable Units

The selective manipulation of Hyp customizable units in DKP substrates allows the generation of a rigid scaffold with four tailor‐made chains which are spatially‐orientated. The key step is a domino radical scission‐oxidation process which allows the generation of N‐substituted DKPs. The versatility...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-08, Vol.362 (15), p.3158-3169
Main Authors: Saavedra, Carlos J., Cuevas, Fernando, Romero‐Estudillo, Ivan, Boto, Alicia
Format: Article
Language:English
Subjects:
Chains
chemoselectivity
Cleavage
domino reactions
organic synthesis
Oxidation
peptides
Scaffolds
Substrates
sustainable chemistry
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Summary:The selective manipulation of Hyp customizable units in DKP substrates allows the generation of a rigid scaffold with four tailor‐made chains which are spatially‐orientated. The key step is a domino radical scission‐oxidation process which allows the generation of N‐substituted DKPs. The versatility of this methodology to produce scaffolds in high optical purity for material and drug discovery is described herein.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000470