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CtD strategy to construct stereochemically complex and structurally diverse compounds from griseofulvin.

Li Zhu1, Rui-Han Zhao2, Yu Li1

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This summary is machine-generated.

The Complexity to Diversity strategy synthesized a 47-compound collection from griseofulvin. Novel tandem reactions generated complex, ring-fused molecules, expanding synthetic chemistry capabilities.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • The Complexity to Diversity (CtD) strategy enables the synthesis of diverse small molecules from natural products.
  • Ring-distortion reactions are key to the CtD strategy for generating molecular complexity.
  • Griseofulvin serves as a valuable natural product starting material for synthetic diversification.

Purpose of the Study:

  • To apply the CtD strategy for synthesizing a diverse compound library.
  • To explore novel tandem reactions within the CtD framework.
  • To generate stereochemically complex, ring-fused compounds from griseofulvin.

Main Methods:

  • Application of the Complexity to Diversity (CtD) strategy.
  • Utilizing ring-distortion reactions for molecular synthesis.
  • Employing a Tsuji-Trost allylation and oxa-Michael cyclization tandem reaction for the first time in CtD.

Main Results:

  • A 47-member compound collection was synthesized from the natural product griseofulvin.
  • Complex, ring-fused molecular architectures were successfully generated.
  • The novel tandem reaction proved effective for CtD strategy implementation.

Conclusions:

  • The CtD strategy, augmented by novel tandem reactions, is effective for generating molecular diversity.
  • This approach expands the synthetic utility of natural products like griseofulvin.
  • The study demonstrates a new method for creating complex ring-fused compounds.