Synthesis of Peptidomimetics via IMCR/Post-Transformation Strategy

Abstract

A series of three 2,5-Diketopiperazine (DKP's) were synthesized via one-pot process through the post-IMCR-transformation strategy. This strategy emphasizes the role of orthogonal bifunctional reagents in the IMCR process to increase their synthetic potential, allowing us accessing a synthetic platform from which it is possible to obtain privileged heterocyclic peptidomimetics via lactamization reaction.

Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

“…The C-C disconnection ( Scheme 1 , C) often involves enolate acylation, albeit radical routes were also described to attain the C-C cyclization [ 63 ]. Despite the various synthetic routes available, the search is still active in this area with new developments pertaining to CDP synthesis appearing also in the most recent literature [ 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 ].…”

Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions

“…[ 6 , 7 ]. Among IMCRs, long standing Ugi four-component reaction (U-4CR) leads to diversely substituted peptidomimetic backbones starting from abundantly available building blocks and, in combination with subsequent cyclization reactions, has become a valuable tool in the design and synthesis of cyclic constrained peptidomimetics and heterocyclic compounds [ 8 , 9 ], also contributing in recent years to the emergence of many important drugs for the treatment of several diseases [ 10 ]. By tactical application of multi-functionalized building blocks and combination with other prominent synthetic strategies, such as ring closing metathesis [ 11 ] or Pd-catalyzed reactions [ 12 ], high molecular diversity can be rapidly achieved by IMCRs [ 13 ], establishing their relevance also in the total synthesis of complex natural products [ 14 ].…”