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Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.

Paul P Sinclair1, Richmond Sarpong1

  • 1Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720, United States.

Angewandte Chemie (International Ed. in English)
|July 12, 2024
PubMed
Summary

This study reports the first total synthesis of baphicacanthcusine A, a complex natural product. The novel synthesis features diastereoselective methods for creating pseudoindoxyl structures, paving the way for related alkaloid synthesis.

Keywords:
alkaloidsoxidationsrearrangementsring contractionstotal synthesis

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Baphicacanthcusine A is a poly-pseudoindoxyl natural product with potential biological activity.
  • The complex structure of baphicacanthcusine A presents a significant synthetic challenge.
  • Previous synthetic efforts have not achieved the total synthesis of this compound.

Purpose of the Study:

  • To achieve the first total synthesis of baphicacanthcusine A.
  • To develop novel synthetic methodologies for constructing poly-pseudoindoxyl alkaloids.
  • To explore the chemical space around baphicacanthcusine A for potential drug discovery.

Main Methods:

  • Leveraging oxidative rearrangement of indoles to pseudoindoxyls.
  • Employing an acid-mediated cyclization/indole transposition.
  • Utilizing diastereoselective oxidative ring contractions and site-selective C-H oxygenation.

Main Results:

  • Successful completion of the first total synthesis of baphicacanthcusine A.
  • Demonstration of a diastereoselective method for installing vicinal pseudoindoxyl heterocycles.
  • Identification of a hidden symmetry element guiding the synthesis of oxidation precursors.

Conclusions:

  • The developed synthetic strategy provides a robust foundation for accessing baphicacanthcusine A and related poly-pseudoindoxyl alkaloids.
  • This work expands the synthetic toolkit for natural product synthesis.
  • The synthetic route may enable further biological evaluation of baphicacanthcusine A and its analogs.