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Updated: May 28, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Stereoselective total synthesis of aminoiminohexitols via carbamate annulation
Anna L Win-Mason1, Seino A K Jongkees, Stephen G Withers
1School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand.
Abstract:
New methodology for the preparation of a variety of aminoiminohextitols is described. Key in the synthesis is the application of a diastereoselective Strecker reaction and the extension of our carbamate annulation methodology to protected and functionalized alkenylamines. Insight into the effects that the substitution patterns of the alkenylamines have on the diastereoselectivity of the iodocyclization and carbamate annulation is discussed. An evaluation of the glycosidase inhibitory activity of the aminoiminohexitols and derivatives is also presented, with the previously undisclosed D-talo isomer showing good selective inhibition of β-D-glucosidase.
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