Synthesis of 3-epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow

28 February 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A total 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 core and an intramolecular Mukaiyama aldol reaction. The synthesis features a late-stage photo-oxidation of a methoxyallene intermediate for the installation of an ester functionality. Problems encountered during the batch process were solved by translation of the transformation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging steps in natural product synthesis.


Total Synthesis
Natural Products
Flow Chemistry

Supplementary materials

Supporting Information
Synthetic Procedures, Spectra, HPLC, X-ray


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