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Synthesis and Late-Stage Modification of (-)-Doliculide Derivatives Using Matteson's Homologation Approach.

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|April 26, 2024
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(-)-Doliculide, a marine cyclodepsipeptide from Dolabella auricularia, shows strong cytotoxic effects. Matteson

Keywords:
Matteson homologationSAR studiesactin binderclick chemistrydoliculide

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Area of Science:

  • Marine natural products chemistry
  • Synthetic organic chemistry

Background:

  • (-)-Doliculide is a marine cyclodepsipeptide isolated from Dolabella auricularia.
  • It possesses potent cytotoxic properties, making it a target for chemical synthesis.

Purpose of the Study:

  • To explore the synthetic accessibility of (-)-Doliculide.
  • To utilize Matteson's homologation for polyketide side chain diversification.
  • To enable late-stage functionalization for structure-activity relationship studies.

Main Methods:

  • Application of Matteson's homologation methodology.
  • Synthesis of the polyketide moiety of (-)-Doliculide.
  • Late-stage functionalization strategies.

Main Results:

  • Demonstrated the feasibility of synthesizing (-)-Doliculide.
  • Successfully diversified the polyketide side chain.
  • Enabled modifications for SAR studies.

Conclusions:

  • (-)-Doliculide synthesis is achievable.
  • Matteson's homologation is effective for polyketide diversification.
  • The synthetic route facilitates SAR investigations of cytotoxic marine compounds.