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A Concise Route to the Strongylophorines.

Wanwan Yu1, Per Hjerrild1, Jacob Overgaard1

  • 1Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.

Angewandte Chemie (International Ed. in English)
|May 31, 2016
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Summary

Researchers report an efficient eight-step semisynthesis of strongylophorine-2, a class of bioactive natural products. This novel route provides access to six related compounds, marking the first synthetic entry into this chemical family.

Keywords:
C−H activationcascade reactionscyclizationnatural productssemisynthesis

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Strongylophorines are a class of bioactive polycyclic meroterpenoids.
  • Previous synthetic routes to strongylophorines were limited or non-existent.
  • Isocupressic acid is an abundant natural product that can serve as a starting material.

Purpose of the Study:

  • To develop an efficient semisynthetic route to strongylophorine-2.
  • To establish the first synthetic entry into the strongylophorine class of natural products.
  • To enable access to a broader range of strongylophorine analogues for further study.

Main Methods:

  • An eight-step semisynthesis utilizing isocupressic acid as a starting material.
  • Key transformations include an iron(III)-mediated rearrangement-cyclization cascade.
  • A directed photochemical sp(3) C-H δ-lactonization was employed for cyclization.

Main Results:

  • Successful synthesis of strongylophorine-2 in eight steps.
  • The developed route provides access to six additional strongylophorine family members.
  • Demonstrated the feasibility of using isocupressic acid as a readily available building block.

Conclusions:

  • The reported semisynthesis is an efficient and novel approach to strongylophorines.
  • This work opens avenues for the synthesis of diverse bioactive meroterpenoids.
  • The methodology provides a platform for exploring the biological activities of strongylophorine analogues.