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This study explores bioinspired synthesis for efficient natural product synthesis and skeletal diversification. Researchers mimicked biosynthetic pathways to achieve concise total syntheses and create diverse natural product libraries.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Bioorganic Chemistry

Background:

  • Current challenges in total synthesis include improving efficiency and enabling divergent synthesis of natural products.
  • Bioinspired synthesis is a recognized strategy for enhancing synthetic efficiency.
  • Late-stage skeletal diversification using bioinspired approaches shows promise for generating diverse natural products.

Purpose of the Study:

  • To summarize the laboratory's endeavors in the bioinspired synthesis of natural products.
  • To categorize and showcase methods based on mimicking biosynthetic reactions and processes.
  • To demonstrate the application of bioinspired synthesis for both efficient total synthesis and skeletal diversification.

Main Methods:

  • Mimicking key cyclization steps in biosynthetic pathways to develop rapid and efficient core skeleton construction methods.
  • Proposing and investigating alternative biosynthetic pathways when current ones contradict chemical principles.
  • Imitating biogenic skeletal diversification processes for divergent synthesis of natural products with distinct carbon skeletons.

Main Results:

  • Achieved concise total syntheses of several natural products, including lamellarins D and H, clavicipitic acid, phalarine, α-cyclopiazonic acid, and speradine C, using bioinspired reactions.
  • Successfully synthesized euphorikanin A via a bioinspired benzilic acid-type rearrangement and bipolarolides A and B via a bioinspired Prins reaction/ether formation cascade.
  • Demonstrated divergent total syntheses of ten pallavicinia diterpenoids and six grayanane diterpenoids with distinct skeletons, showcasing unprecedented ease and efficiency.

Conclusions:

  • Bioinspired synthesis is a powerful strategy for overcoming challenges in natural product total synthesis.
  • Mimicking biosynthetic pathways, including key cyclizations and skeletal diversification, enables efficient and diverse synthesis.
  • The demonstrated bioinspired skeletal diversification strategy can inspire the synthesis of other complex, skeletally diverse natural products.