Oxidative cleavage (OsO/NaIO) of a monoprotected dihydroxy sulfinyl diene affords a lactol, readily transformed into a sulfinyl pyranose. Alternatively, base promoted intramolecular cyclization of a lactol derived carbamate to a bicyclic oxazolidinone followed by simple transformations leads to an amino sulfonyl pyranose. In contrast, ozonolysis of a variety of hydroxy sulfinyl dienes leads to fair yields of 3-sulfinyl furans in a single step.

This research was supported by grants CTQ2009-07752 and CTQ2016-77555-C2-2-R. We thank CSIC-FSE for a doctoral fellowship to A.C. and a postdoctoral contract to I.O.

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