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Feigrisolide C: structural revision and synthesis.

Woo Han Kim1, Jae Hoon Jung, Eun Lee

  • 1Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.

The Journal of Organic Chemistry
|November 10, 2005
PubMed
Summary
This summary is machine-generated.

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The structure of feigrisolide C was revised from its original macrodiolide proposal. Total synthesis confirmed the correct structure as a homononactoyl nonactic acid derivative.

Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis

Background:

  • Feigrisolide C was initially characterized with an incorrect macrodiolide structure.
  • Accurate structural elucidation is crucial for understanding natural product bioactivity.

Purpose of the Study:

  • To determine the correct chemical structure of feigrisolide C.
  • To validate the proposed structure through total synthesis.

Main Methods:

  • Spectroscopic analysis (NMR, MS) for structural determination.
  • Chemical synthesis to construct the proposed feigrisolide C molecule.

Main Results:

  • The macrodiolide structure was disproven.
  • The correct structure was identified as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid.

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  • Total synthesis successfully yielded the revised structure, confirming its identity.

    • Conclusions:

    • The original structural assignment of feigrisolide C was erroneous.
    • The confirmed structure provides a basis for future studies on feigrisolide C's properties and biological roles.