An efficient asymmetric synthesis of grenadamide |
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Authors: | Rachel Green Sarah Duffill Steven D. Bull |
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Affiliation: | a Department of Chemistry, University of Bath, Bath BA2 7AY, UK b GlaxoSmithKline Research and Development, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK |
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Abstract: | The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the β-hydroxyl group of a syn-aldol product as a ‘temporary’ stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. |
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Keywords: | syn-aldol Cyclopropanation β-Elimination Temporary stereocentre Natural product |
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