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Gram‐Scale Synthesis of the (−)‐Sparteine Surrogate and (−)‐Sparteine
Authors:Dr. James D. Firth  Dr. Steven J. Canipa  Dr. Leigh Ferris  Prof. Peter O'Brien
Affiliation:1. Department of Chemistry, University of York, York, UK;2. AstraZeneca (UK), Macclesfield, Cheshire, UK
Abstract: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.
Keywords:alkaloids  asymmetric synthesis  kinetic resolution  nitrogen ligands  total synthesis
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