Gram-Scale Synthesis of the (-)-Sparteine Surrogate and (-)-Sparteine

James D Firth, Steven J Canipa, Peter O'Brien, Leigh Ferris

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An 8-step, gram-scale synthesis of the (-)-sparteine surrogate (22% yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (-)-sparteine (31% yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.

Original languageEnglish
Pages (from-to)223-226
Number of pages4
JournalAngewandte Chemie International Edition
Issue number1
Early online date20 Nov 2017
Publication statusPublished - 2 Jan 2018

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  • Journal Article
  • asymmetric synthesis
  • alkaloids
  • kinetic resolution
  • total synthesis
  • nitrogen ligands

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