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A concise total synthesis of salinosporamide A

Nicholas P Mulholland1, Gerald Pattenden, Iain A S Walters

  • 1School of Chemistry, University of Nottingham, England, UK. GP@nottingham.ac.uk

Organic & Biomolecular Chemistry
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PubMed

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...