Synthesis and Structural Revision of Glyphaeaside C

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Synthesis and Structural Revision of Glyphaeaside C

Byatt, Brendan J; Kato, Atsushi; Pyne, Stephen G

Organic letters, 05/2021, Volume: 23, Issue: 10

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The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

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Byatt, Brendan J | Kato, Atsushi | Pyne, Stephen G

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