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Diketomorpholines (DKMs), a class of cyclodepsipeptides, are versatile six-membered ring compounds. This review highlights their synthesis and application in ring-opening polymerization, noting their presence in natural products.

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Natural Product Synthesis

Background:

  • Diketomorpholines (DKMs), also known as morpholine-2,5-diones, are cyclic compounds featuring both lactone and lactam functionalities.
  • DKMs are classified within the broader family of cyclodepsipeptides, known for their diverse biological activities and structural complexity.
  • The DKM scaffold is found in various natural products, ranging from simple monocyclic structures to intricate polycyclic systems with fused DKM rings.

Purpose of the Study:

  • To provide a comprehensive summary of the synthetic methodologies available for constructing diketomorpholine scaffolds.
  • To emphasize the significant utility of diketomorpholines, particularly in the context of ring-opening polymerization (ROP) reactions.
  • To review the occurrence and structural diversity of DKMs within the realm of natural products.

Main Methods:

  • Literature review focusing on synthetic routes to diketomorpholines.
  • Analysis of published research on the application of DKMs in polymerization.
  • Survey of natural product databases and literature for DKM-containing compounds.

Main Results:

  • The review consolidates various synthetic strategies for accessing the diketomorpholine core structure.
  • Diketomorpholines are demonstrated to be effective monomers or initiators in ring-opening polymerization, leading to novel polymer architectures.
  • A wide array of natural products incorporating the diketomorpholine moiety, from simple to complex structures, has been identified.

Conclusions:

  • Diketomorpholines represent a synthetically accessible and versatile class of cyclodepsipeptides.
  • Their application in ring-opening polymerization offers a valuable route to functional polymers.
  • The prevalence of DKMs in nature underscores their biological relevance and potential for further discovery.