A Short Synthesis of (±)-3-Demethoxyerythratidinone by Ligand-Controlled Selective Heck Cyclization of Equilibrating
Emma E Blackham1, Kevin I Booker-Milburn1
1School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Abstract:
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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