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PreprintCC BYChemRxiv

Concise Total Synthesis of (–)-5-epi-Cycloclavine via Metal- and Base-Free Diastereoselective

  • Francesca Diotallevi1
  • Francesca Bartoccini1
  • Giovanni Piersanti1
  1. 1Department of Biomolecular Sciences, University of Urbino Carlo Bo, Via Ca’ Le Suore 2, Urbino, Italy
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Abstract

A metal- and base-free intramolecular cyclopropanation based on nonstabilized donor carbenes generated in situ from N-sulfonylhydrazones has been developed, enabling the construction of the highly strained aza[3.1.0]bicyclic core of (–)-5-epi-cycloclavine with concomitant complete stereocontrol of two all-carbon quaternary stereocenters. Combined with the straightforward introduction of methacrylic acid as four-carbon fragment from readily available enantiopure functionalized tricyclic indole derivative (4-amino Uhle's ketone), this strategy enabled a concise diasteroselective synthesis of the five-fused rings system present in (–)-5-epi-cycloclavine.

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Cite

BibTeXRIS
BibTeX
@misc{diotallevi2026concise,
  title = {{Concise Total Synthesis of (–)-5-epi-Cycloclavine via Metal- and Base-Free Diastereoselective}},
  author = {Francesca Diotallevi and Francesca Bartoccini and Giovanni Piersanti},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008870/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008870/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Concise Total Synthesis of (–)-5-epi-Cycloclavine via Metal- and Base-Free Diastereoselective
AU  - Francesca Diotallevi
AU  - Francesca Bartoccini
AU  - Giovanni Piersanti
PY  - 2026
DA  - 2026/09/15
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008870/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008870/v1
AB  - A metal- and base-free intramolecular cyclopropanation based on nonstabilized donor carbenes generated in situ from N-sulfonylhydrazones has been developed, enabling the construction of the highly strained aza[3.1.0]bicyclic core of (–)-5-epi-cycloclavine with concomitant complete stereocontrol of two all-carbon quaternary stereocenters. Combined with the straightforward introduction of methacrylic acid as four-carbon fragment from readily available enantiopure functionalized tricyclic indole derivative (4-amino Uhle's ketone), this strategy enabled a concise diasteroselective synthesis of the five-fused rings system present in (–)-5-epi-cycloclavine.
ER  -