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This is an example of the reaction of a ketone with a Grignard reagent, which gives a tertiary alcohol. The paper presents a study of several different idol-3-ones reacting with Grignard reagents. Idol-3-ones are potentially useful intermediates in the synthesis of alkaloids and pharmaceutical agents.
Going one step further: due to the lack of stability in the tertiary alcohol, a rearrangement is observed on the alcohol molecule, creating a gain in resonance stabilization in the final molecule. The study examined a variety of conditions under which the rearrangement occurred, in order to recognize the most efficient one. It was determined that the rearrangement took place with great facility under acidic or basic conditions or was thermally induced.

The above is one of the final reactions in the synthesis of an enantiospecifically labeled fatty acid. It involves a reduction with Lindlar’s Catalyst in the presence of deuterium, an isotope of hydrogen. Lindlar’s Catalyst (powdered barium sulfate coated with Pd, poisoned with quinoline) converts an alkyne to a cis-alkene, as seen in the reaction above. The article I looked at focused on pheromone biosynthesis in S. isatideus and the role stereochemistry played.

The main protocol for the synthesis of β-alkoxy alcohols is the alcoholysis of 1,2-epoxides. To synthesize epoxides, we can use oxone in the presence of transition metal complexes, or cyclodextrines, or via the formation of dioxiranes.

An application of this type of reaction is the synthesis of β-methoxy alcohols. It is done by the one-pot reaction of alkenes with oxone in methanol without any other catalyst.

Note: Oxone (2KHSO5·KHSO4·K2SO4) is the registered trademark from Du Pont.

General reaction and some examples are shown above.

This is one of the steps in the synthesis of Taxol. Taxol is an anticancer drug found in the bark of the Pacific yew tree. In the step outlined, an ester is reduced by LiAlH4 and THF to an alcohol.

Let’s look at some chemical structures:
One problem occurs with aspirin is that it has a destructive effect on the blood vessel walls and inhibit the synthesis of prostacyclin. To resolve this problem, we can use potential anti-platelet agents including the O-acyl esters which are synthesized from salicylic acid and diflunisal. Those agents work by acylation of cyclooxygenase and have a higher extraction than aspirin. That makes them yield a greater selectivity in their effect on platelet inhibition relative to prostacyclin inhibition on vessel walls.

The actual reaction is shown on the top.