Synthesis and Structural Revision of Glyphaeaside C
Publication Name
Organic Letters
Abstract
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.
Open Access Status
This publication is not available as open access
Volume
23
Issue
10
First Page
4029
Last Page
4033
Funding Number
DP 130101968
Funding Sponsor
Australian Research Council