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A Route to (2α,3β,4α)-(±)-2-(Hydroxymethyl)-3,4-pyrrolidinediol Based on the α-Silyloxyallylation of a Glycolaldehyde-Derived Nitrone

✍ Scribed by Marco Lombardo; Simone Spada; Claudio Trombini

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
151 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

A protected form of title compound 6a, whose two which, after O-silylation, was subjected to iodocyclisation to give 5-iodomethylisoxazolidine 7a as a single diastereo-enantiomers are known to be potent α-glycosidase inhibitors, was obtained through a five-step synthesis based on two isomer. Displacement of iodide by mesylate and hydrogenolysis of mesylate 7b furnished 6b in 20 % overall thoroughly diastereo-controlled steps. An anti-selective αsilyloxyallylation of nitrone 9 afforded hydroxylamine 8a yield starting from tert-butyldimethylsilyloxyacetaldehyde.

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