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. Author manuscript; available in PMC: 2013 Apr 18.
Published in final edited form as: J Am Chem Soc. 2012 Apr 10;134(15):6552–6555. doi: 10.1021/ja301723p

Scheme 1.

Scheme 1

Fluorosugars 2 and 3 can be accessed from a common intermediate, vinyl furanose 4 (top). A kinetically controlled separation of epoxide diastereomers can be used as a synthetic divergence point and as a method to isolate stereodefined isomers 8 and 9 en route to the synthetic targets.