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PreprintCC BYChemRxiv

Ten-Step Total Synthesis of the Octadride (+)-Zopfiellin via Electrochemical Decarboxylative Cross-Coupling

  • Adrien Merviel1,2
  • Michael Seidl3,2
  • Thomas Magauer1,2
  1. 1Department of Organic Chemistry and Center for Molecular Biosciences
  2. 2University of Innsbruck
  3. 3Department of General, Inorganic & Theoretical Chemistry
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Abstract

We report the first asymmetric total synthesis of the antifungal octadride natural products zopfiellin and deoxyzopfiellin. Our highly convergent synthetic strategy features a bioinspired electrochemical nickel-catalyzed decarboxylative cross-coupling of two readily available fragments to assemble the core skeleton. This key transformation enables a subsequent intramolecular alkylation, forging the eight-membered carbocycle with excellent diastereoselectivity. Notably, the protecting-group-free route is robust and scalable, providing access to (+)-zopfiellin in 10 steps.

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Cite

BibTeXRIS
BibTeX
@misc{merviel2026tenstep,
  title = {{Ten-Step Total Synthesis of the Octadride (+)-Zopfiellin via Electrochemical Decarboxylative Cross-Coupling}},
  author = {Adrien Merviel and Michael Seidl and Thomas Magauer},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010978/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010978/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Ten-Step Total Synthesis of the Octadride (+)-Zopfiellin via Electrochemical Decarboxylative Cross-Coupling
AU  - Adrien Merviel
AU  - Michael Seidl
AU  - Thomas Magauer
PY  - 2026
DA  - 2026/10/23
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010978/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010978/v1
AB  - We report the first asymmetric total synthesis of the antifungal octadride natural products zopfiellin and deoxyzopfiellin. Our highly convergent synthetic strategy features a bioinspired electrochemical nickel-catalyzed decarboxylative cross-coupling of two readily available fragments to assemble the core skeleton. This key transformation enables a subsequent intramolecular alkylation, forging the eight-membered carbocycle with excellent diastereoselectivity. Notably, the protecting-group-free route is robust and scalable, providing access to (+)-zopfiellin in 10 steps.
ER  -