Synlett 1998; 1998(5): 554-556
DOI: 10.1055/s-1998-1698
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The Synthesis of Deoxygalactostatin and 2,6-Imino-heptitol Derivatives via Stannane Mediated Hydroxymethylation of 5-Azido-1,4-lactones

John P. Shilvock* , George W. J. Fleet
  • *Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford OX1 3QY, UK; Fax + 44-1865-27 74 35; E-mail: george.fleet@chemistry.ox.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Deoxygalactostatin, homogalactonojirimycin derivatives and other 2,6-imino-heptitols are accessed via the nucleophilic addition of a hydroxymethyl anion equivalent to 5-azido-1,4-lactones to afford 6-azido-lactols. Subsequent hydrogenation induces intramolecular reductive amination to produce the desired piperidine ring systems.

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