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