through hydrogen-bonding interactions, thus facilitating regioselective deprotonation by triethylamine. The silyl enol ether was then treated with excess mCPBA to facilitate a “double” Rubottom oxidation to give the exo product with both hydroxyl groups on the outside of the fused ring system. This dihydroxy product was then transformed into Velutinol A in three additional steps. The Clive group utilized the Rubottom oxidation in the synthesis of an advanced intermediate for their degradation studies of the cholesterol-lowering fungal metabolite mevinolin. This interesting sequence features the addition of excess n-butyllithium (BuLi) in the presence of lithium diisopropylamide (LDA) for full conversion of the bicyclic ketone derivative to the corresponding silyl enol ether. Without BuLi the authors report a maximum yield of only 72%. Subsequent buffered Rubottom oxidation conditions with sodium bicarbonate in ethyl acetate afforded the α-hydroxy ketone as a single diastereomer. The Falk group synthesized various derivatives of phosphatidyl-D-myo-inositol to aid in the study of the various phosphatidylinositol 3-kinase (PI3K) cell signaling pathways. Their route to the collection of substrate analogs exploits a substrate-controlled stereoselective Rubottom oxidation using dimethyl dioxirane(DMDO) as the oxidant and catalytic camphorsulfonic acid (CSA) to aid in hydrolysis. For protecting groups see ref Problems and shortcomings While the Rubottom oxidation generally gives good yields and is highly scalable (see 2S-hydroxymutilin synthesis), there are still some problems with the reaction. As mentioned above, the acidic reaction conditions are not tolerated by many complex substrates, but this can be abrogated with the use of buffer systems. Poor atom economy is also a major issue with the reaction because it requires stoichiometric oxidant, which generates large amounts of waste. Peroxides can also be dangerous to work with. mCPBA is known to detonate from shock or sparks. α-Hydroxylation of related compounds Although silyl enol ethers of aldehydes and ketones are the traditional substrates for the Rubottom oxidation, as mentioned above, silyl ketene acetals and bis (silyl acetals) can be oxidized to their α-hydroxy ester or carboxylic acid derivatives using lead(IV) acetate or hypofluorous acid-acetonitrile (HOF–ACN). However, these α-hydroxylations do not proceed via silyl enol ether intermediates and are therefore not technically Rubottom oxidations. Various oxidants can be used to oxidize many of these carbonyl derivatives after they are converted to their respective enolate or related anion. Some common oxidants are peroxy acids, molecular oxygen, and hypervalent iodine reagents. References Bibliography Kürti, L.; Czakó, B. (2005) Strategic Applications of Named Reactions in