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Concise Syntheses of Violaceoids A and C.

Koichi Narita1, Ryuhei Kimura1, Hiroka Satoh1

  • 1Laboratory of Synthetic and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University.

Chemical & Pharmaceutical Bulletin
|November 26, 2020
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Summary

Researchers developed a protecting-group-free synthesis for natural products violaceoids A and C. This novel method efficiently introduces alkenyl side chains using alkenylboronic acid, marking the first synthesis of violaceoid C.

Keywords:
alkylated hydroquinoneprotecting-group-free synthesistotal synthesisviolaceoid

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • Alkylated hydroquinones are a class of natural products with potential biological activities.
  • Efficient synthetic routes to these compounds are valuable for further study.

Purpose of the Study:

  • To develop a concise and protecting-group-free synthesis of violaceoids A and C.
  • To establish a novel method for introducing alkenyl side chains in natural product synthesis.

Main Methods:

  • A protecting-group-free synthetic strategy was employed.
  • 2,5-dihydroxybenzaldehyde was used as the starting material.
  • Alkenylboronic acid served as a key reagent for coupling and temporary protection.

Main Results:

  • Successful and concise syntheses of violaceoids A and C were achieved.
  • The method efficiently introduced the alkenyl side chain of violaceoid A.
  • The synthesis of violaceoid C was reported for the first time.

Conclusions:

  • A novel and efficient protecting-group-free synthetic route to violaceoids A and C has been established.
  • The use of alkenylboronic acid offers a versatile strategy for natural product synthesis.
  • This work provides access to previously unsynthesized violaceoid C.