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Employing Pressurized Hot Water Extraction PHWE to Explore Natural Products Chemistry in the Undergraduate Laboratory
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Total Synthesis of Hyperforin.

Chi P Ting1, Thomas J Maimone1

  • 1Department of Chemistry, University of California , Berkeley, California 94720, United States.

Journal of the American Chemical Society
|August 8, 2015
PubMed
Summary

Researchers report a 10-step synthesis of hyperforin, a natural product, using a novel diketene annulation and oxidative ring expansion. This method efficiently creates a key bicyclo[3.3.1]nonane-1,3,5-trione structure for diverse polyprenylated acylphloroglucinol synthesis.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Hyperforin is a key bioactive natural product belonging to the polyprenylated acylphloroglucinol (PPAP) class.
  • Existing synthetic routes to hyperforin and related PPAPs are often lengthy and complex.
  • Understanding the biosynthesis of meroterpenes like hyperforin can inform synthetic strategies.

Purpose of the Study:

  • To develop an efficient and concise total synthesis of hyperforin.
  • To establish a versatile platform for the synthesis of diverse PPAP analogues.
  • To explore novel synthetic methodologies applicable to complex natural products.

Main Methods:

  • A 10-step total synthesis commencing from 2-methylcyclopent-2-en-1-one.
  • Utilized a key diketene annulation reaction for core structure construction.

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  • Employed an oxidative ring expansion strategy to achieve the target polycyclic system.

    • Main Results:

    • Successful 10-step total synthesis of hyperforin.
    • Efficient preparation of a highly substituted bicyclo[3.3.1]nonane-1,3,5-trione motif in six steps.
    • Demonstrated a versatile platform for generating diverse and modifiable PPAPs.

    Conclusions:

    • The developed synthetic route provides a streamlined approach to hyperforin.
    • The methodology enables facile access to a wide array of structurally diverse PPAPs.
    • This work facilitates further investigation into the biological activities of hyperforin analogues.