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Total synthesis of cynaropicrin.

Tenma Nakamura1, Dinda B Pitna1, Kogaku Kimura1

  • 1Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan. t-usuki@sophia.ac.jp.

Organic & Biomolecular Chemistry
|May 13, 2021
PubMed
Summary

Researchers achieved the first total synthesis of cynaropicrin, a bitter compound from artichokes. This breakthrough utilized stereoselective reactions, paving the way for further study of its biological activities.

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Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Cynaropicrin, a sesquiterpene lactone found in artichoke (Cynara scolymus), imparts a bitter taste.
  • This natural product exhibits significant biological activities, including inhibition of NF-κB activation, anti-hepatitis C, and antitrypanosomal effects.
  • The complex structure of cynaropicrin, featuring a 5-7-5 tricyclic skeleton, six chiral centers, and four exo-olefins, presents a synthetic challenge.

Purpose of the Study:

  • To achieve the first total synthesis of the natural product cynaropicrin.
  • To explore novel synthetic strategies for complex sesquiterpene lactones.
  • To provide a scalable route for obtaining cynaropicrin for further biological evaluation.

Main Methods:

  • The total synthesis commenced from (S)-α-pinene, a readily available chiral starting material.
  • Key synthetic steps included a stereoselective Favorskii rearrangement.
  • An indium-promoted diastereoselective Barbier reaction was employed to construct the molecular framework.

Main Results:

  • The first successful total synthesis of cynaropicrin was accomplished.
  • The synthetic route demonstrated high stereoselectivity and diastereoselectivity.
  • The study provides a validated pathway for the preparation of cynaropicrin.

Conclusions:

  • The total synthesis of cynaropicrin has been successfully realized.
  • The developed synthetic methodology offers a valuable approach for accessing complex sesquiterpene lactones.
  • This synthesis enables further investigation into the medicinal potential of cynaropicrin.