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

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

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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    Rights statement: This is the final published version of the article (version of record). It first appeared online via Wiley at http://onlinelibrary.wiley.com/doi/10.1002/anie.201701775/abstract. Please refer to any applicable terms of use of the publisher.

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