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Total Syntheses of Asperchalasines A-E.

Ruiyang Bao1, Chong Tian1, Haoyu Zhang1

  • 1School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Tsinghua University, Beijing, 100084, China.

Angewandte Chemie (International Ed. in English)
|September 8, 2018
PubMed
Summary

This study reports the first total syntheses of novel merocytochalasans, asperchalasin A-E. Key synthetic strategies include Diels-Alder reactions and ring-closing metathesis for constructing the complex cytochalasan structures.

Keywords:
Diels-Alder reactionsbiomimetic synthesiscycloadditionsdimerizationnatural products

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Merocytochalasans are a class of complex natural products with potential biological activities.
  • The total synthesis of these compounds presents significant chemical challenges.
  • Previous synthetic efforts have not achieved the complete assembly of asperchalasines A-E.

Purpose of the Study:

  • To achieve the first total synthesis of asperchalasines A-E.
  • To develop efficient synthetic routes for constructing the tricyclic cytochalasan monomer, aspochalasin B.
  • To explore bioinspired and biomimetic strategies for assembling complex merocytochalasans.

Main Methods:

  • Unified synthetic approach for aspochalasin B utilizing Diels-Alder and ring-closing metathesis reactions.
  • Bioinspired Diels-Alder reactions between aspochalasin B and epicoccine precursors for heterodimer synthesis.
  • Biomimetic Diels-Alder and oxidative [5+2]-cycloaddition for heterotrimer synthesis.

Main Results:

  • Successful total synthesis of aspochalasines A-E.
  • Efficient construction of the tricyclic cytochalasan monomer, aspochalasin B.
  • Divergent synthesis of heterodimers (asperchalasines B-E) and a heterotrimer (asperchalasin A) through strategic cycloaddition reactions.

Conclusions:

  • The developed synthetic strategies provide access to unprecedented merocytochalasans.
  • The study highlights the utility of Diels-Alder and metathesis reactions in complex molecule synthesis.
  • This work lays the foundation for further exploration of merocytochalasans' biological properties.