Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and ‘Guanidine’ Isofagomine

Peter J. Meloncelli; Robert V. Stick

doi:10.1071/CH06241

RESEARCH ARTICLE

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Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and ‘Guanidine’ Isofagomine

Peter J. Meloncelli ^A and Robert V. Stick ^A ^B

+ Author Affiliations

- Author Affiliations

^A Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia.

^B Corresponding author. Email: rvs@chem.uwa.edu.au

Australian Journal of Chemistry 59(11) 827-833 https://doi.org/10.1071/CH06241
Submitted: 11 July 2006 Accepted: 25 September 2006 Published: 17 November 2006

Abstract

Improvements in the preparation of a key imidazylate and the reduction of the derived nitrile have led to more efficient syntheses of isofagomine, noeuromycin, azafagomine, and isofagomine lactam. As well, a precursor of azafagomine has been converted into azanoeuromycin, and the nitrogen atom of isofagomine has been incorporated into a guanidine residue.

Acknowledgments

We thank Ian D. Jenkins for suggesting the guanidine 6 as an interesting synthetic target, and Gideon Davies and Tracey Gloster for investigating its potential as an inhibitor of glycosidases.

References

Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and ‘Guanidine’ Isofagomine

Abstract

Acknowledgments

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