Oxidative Cleavage of Vicinal Diols in the Carbon Framework

Oxidative Cleavage of Vicinal Diols in the Carbon Framework 

Periodate promoted cleavage of vicinal diols has also been used to prepare monocyclic products. Oxabicyclo[4.2.1]nonadiene 116 derived from diiodoke-tone 77 was subjected to sodium periodate and sodium borohydride reduction to generate 117, Eq. 87. Subsequent elaborations resulted in the stereocontrolled synthesis of oxepine 118, a subunit designed for the assembly of polyether toxins such as ciguatoxin [135]. 

Periodate cleavage of dihydroxy oxabicyclic substrate 119 generated an unsymmetrical subunit useful for polyether assembly, Eq. 88 [88]. 

Periodate cleavage of an oxabicyclic diol was also a key step in the synthesis of citreoviral from the Diels-Alder adduct of 2,4-dimethylfuran and vinylene carbonate [136]. 

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