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A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids.

Organic letters (2013-04-05)
Vijay Dhand, Jason A Draper, Jarod Moore, Robert Britton
RESUMO

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.

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Sigma-Aldrich
Swainsonine, synthetic
Sigma-Aldrich
Swainsonine, from Metarrhizium anisopliae, ≥98% (TLC)