Rhodium-catalyzed formylation of organomercurials: Application to efficient polyol synthesis

[GRAPHICS] The rhodium-catalyzed formylation of organomercurials-a new transformation of organomercurials-is reported. The addition of 0.50 equiv of 1,4-diazabic yclo[2.2.2]octane (DABCO) was found to promote the reaction, and it is post ulated that the DABCO acts as a ligand for mercury. Several examples are pr esented to document the scope of the reaction. This reaction was developed in the context of a larger program focused on the development of efficient strategies for the synthesis of polyol-derived natural products, and an eff icient (8 steps) synthesis of Tolypothrix pentaether that employs this meth odology is reported.