Solid-Supported Synthesis of Putative Peptide β-Turn Mimetics via Ugi Reaction for Diketopiperazine Formation
Authors:
- 13 September 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 4 (6) , 584-590
Abstract
The scope and limitations of the solid-supported synthesis of a bicyclic diketopiperazine, an internal, putative peptide β-turn mimetic, are presented. The 4CC multicomponent Ugi reaction of α-N-Boc-diaminopropionic acid resin ester (an amine input), optically active α-bromoacid, aldehyde, and isocyanide is the key step in the proposed synthetic protocol. Application of cyclitive cleavage as the final step led to desired products in high purity.Keywords
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