Concise Total Synthesis of (–)-5-epi-Cycloclavine via Metal- and Base-Free Diastereoselective
Year: 2026
Type: preprint
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.
Source: ChemRxiv
Institution: University of Urbino
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7213233453