Tamao Kumada oxidation

This reaction, depending on the details of the reaction, is known as the Fleming Oxidation, the Fleming-Tamao Oxidation, the Tamao-Fleming Oxidation, or the Tamao-Kumada Oxidation. 

The Tamao-Kumada and Fleming oxidation reactions involve the oxidation of specific silyl groups to provide a hydroxyl group with retention of configuration.1... 

The Tamao-Kumada and Fleming oxidations have found wide synthetic utility in the oxidation of a variety of silyl groups.6,26 29 However, the true virtue of these reactions lies in the manner in which the silyl group is introduced into the molecule to be oxidized. A number of creative strategies have been developed for this process, some of which will be highlighted below. 

Radical cyclization has also proved to be a useful tool for the Shishido group in their syntheses of triptoquinones B and C and triptocallol.40 Triptoquinone B and C have been shown to exhibit inhibitory activity on interleukin-1 and are both candidates for the treatment of rheumatoid arthritis. Shishido has accomplished synthesis of all three of these compounds, implementing the radical cyclization of bromomethyldimethylsilyl ether 39, derived from optically enriched alcohol 38, to give 40. Finally, the Tamao-Kumada oxidation step provides the natural product, triptocallol (41). 

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