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

Emma E Blackham, Kevin Booker-Milburn

Research output: Contribution to journalArticle (Academic Journal)peer-review

18 Citations (Scopus)
364 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)6613-6616
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number23
Early online date4 May 2017
DOIs
Publication statusPublished - 1 Jun 2017

Structured keywords

  • BCS and TECS CDTs

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