The synthesis of polyhydroxylated 1, 1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1, 5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A ...
