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A short synthesis of hydroxyalkyl dihydropyrroles has been developed that involves the coupling of propargylamines with α-chloroaldehydes, followed by Lindlar reduction and a one-pot epoxide formation/opening sequence. The application of this process to the synthesis of unnatural iminosugars and a formal synthesis of (-)-swainsonine is described.


Vijay Dhand, Jason A Draper, Jarod Moore, Robert Britton. A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids. Organic letters. 2013 Apr 19;15(8):1914-7

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PMID: 23550817

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