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A Short Synthesis of (±)-3-Demethoxyerythratidinone by Ligand Controlled Selective Heck Cyclization of Equilibrating Enamines

Research output: Research - peer-reviewArticle

Original languageEnglish
Number of pages5
JournalAngewandte Chemie - International Edition
Early online date4 May 2017
StateE-pub ahead of print - 4 May 2017


A short, 5-step total synthesis of (±)-3-demethoxyerythratidinone from a simple pyrrole derivative is described. Features include the formation of gram quantities of a key tricylic aziridine from a challenging photochemical cascade reaction through the use of flow photochemistry. The final step involved a highly unusual Heck cyclization whereby ligand control enabled efficient formation of the natural product in 69% yield from the minor isomer present in an equilibrating mixture of labile enamines.

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