Stereoselective total synthesis of aminoiminohexitols via carbamate annulation.
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.
School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand.
Anna L
AL
Win-Mason
Seino A K
SA
Jongkees
Stephen G
SG
Withers
Peter C
PC
Tyler
Mattie S M
MS
Timmer
Bridget L
BL
Stocker
D002219:Carbamates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050112:Imino Pyranoses / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry*
D002219:Carbamates; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D013402:Sugar Alcohols; D006026:Glycoside Hydrolases