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Skeletal Editing Strategies Driven by Total Synthesis.

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Single-atom skeletal editing precisely modifies molecular frameworks, accelerating organic synthesis. This work details methods for ring contractions, expansions, and transpositions in natural product synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Methodology Development

Background:

  • Single-atom skeletal editing offers precise molecular modifications for streamlined organic synthesis.
  • Existing strategies often involve complex rearrangements, motivating the development of more selective methods.
  • Natural product synthesis benefits from efficient strategies that enable challenging retrosynthetic disconnections.

Purpose of the Study:

  • To detail the evolution of skeletal editing logic in natural product total synthesis.
  • To showcase the development of single-atom skeletal editing methodologies for diverse molecular scaffolds.
  • To highlight the application of these methods in simplifying complex molecule synthesis.

Main Methods:

  • Development of single-atom ring contractions, expansions, and transpositions for saturated and unsaturated heterocycles.
  • Leveraging metal-mediated C-C bond cleavage and "break-it-to-make-it" strategies.
  • Application of photomediated and reductive reaction pathways for skeletal modifications.

Main Results:

  • Successful application of skeletal editing in the total synthesis of various natural products, including diterpenoids and alkaloids.
  • Development of methods for selective modification of N-heterocycles, enabling access to distinct natural product families.
  • Cheminformatic analysis guided the development of transformations that expand accessible chemical space.

Conclusions:

  • Single-atom skeletal editing provides a powerful platform for accelerating and simplifying organic synthesis.
  • Continued development of mild, selective, single-step skeletal editing reactions is crucial for complex molecule synthesis.
  • These methodologies hold significant potential for broader applications in organic synthesis and drug discovery.