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Paper | Special issue | Vol 105, No. 1, 2022, pp.500-510
Published online, 12th April, 2022
DOI: 10.3987/COM-22-S(R)21
Oxidative Fragmentation of Cytisine as an Entry to the Bis(piperidine) Scaffold of Virgidivarine

Worawat Niwetmarin* and Timothy Gallagher*

*School of Chemistry, University of Bristol, Bristol BS8 1TS, United Kingdom


Using virgidivarine as a focus, we have extended the oxidative fragmentation of (-)-cytisine as a source of functionalized heterocyclic fragments to provide a novel bis(piperidine) 2-epivirgidivarine. This stereochemically-defined scaffold offers synthetic versatility within an “sp3-rich” environment that makes it amenable to further manipulation and development within the context of de novo drug design.