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Related Experiment Videos

Aruncin B: Synthetic Studies, Structural Reassignment and Biological Evaluation.

Aubert Ribaucourt1, Christopher Towers2, Laia Josa-Culleré1

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 18, 2017
PubMed
Summary

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Structural revision of the cytotoxin aruncin B was necessary due to acid sensitivity. The study reassigned aruncin B as a Z-γ-alkylidenebutenolide and synthesized analogues for biological evaluation.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Aruncin B is a recently isolated cytotoxin with a proposed structure.
  • Initial synthetic attempts revealed unexpected acid sensitivity of the proposed aruncin B structure.
  • Spectroscopic data analysis indicated a need for significant structural reassessment.

Purpose of the Study:

  • To elucidate the correct structure of aruncin B.
  • To develop efficient synthetic routes for aruncin B and its analogues.
  • To evaluate the biological activity of the synthesized compounds.

Main Methods:

  • Ring-closing alkene metathesis (RCM) followed by oxyselenation-selenoxide elimination.
  • Development of a β-iodo Morita-Baylis-Hillman reaction/Sonogashira cross-coupling-5-exo-dig lactonisation sequence.
Keywords:
anticancerbutenolidecytotoxinnatural productsstructure elucidation

Related Experiment Videos

  • Synthesis of Z-γ-alkylidenebutenolide scaffold and analogues.

    • Main Results:

    • The initially proposed structure of aruncin B was revised to a Z-γ-alkylidenebutenolide.
    • A novel synthetic strategy was developed for the revised aruncin B structure.
    • Fourteen γ-alkylidenebutenolide analogues were synthesized alongside aruncin B.

    Conclusions:

    • Aruncin B possesses a Z-γ-alkylidenebutenolide structure, necessitating a significant revision from its initially proposed form.
    • The developed synthetic methodologies provide a flexible platform for generating diverse γ-alkylidenebutenolide analogues.
    • The synthesized compounds are prepared for biological evaluation to assess their cytotoxic potential.