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Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation

TitleStereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
Publication TypeJournal Article
Year of Publication2011
AuthorsWin-Mason, AL, Jongkees, SAK, Withers, SG, Tyler, PC, Timmer, MSM, Stocker, BL
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume76
Pagination9611-9621
Date PublishedDEC 2
ISSN0022-3263
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-taio isomer showing good selective inhibition of beta-D-glucosidase.

DOI10.1021/jo201151b