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Updated: Sep 24, 2025

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Synthesis of 3-epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow
Stefan Leisering1, Sebastian Ponath1, Kamar Shakeri1
1Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
Abstract:
A synthesis of 3-epi-hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, is reported. The carbon skeleton was prepared by functionalization of a cyclopentanone and an intramolecular Mukaiyama aldol reaction. Highlights include a late-stage photo-oxidation of a methoxyallene to provide an ester group. The problems encountered in the batch process were solved by translation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging late-stage transformations in natural product synthesis.
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