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The product of an aldol condensation is an a,b-unsaturated

Chapter 22, Problem 22.88

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QUESTION:

The product of an aldol condensation is an a,b-unsaturated ketone which is capable of undergoing hydrogenation to yield a saturated ketone. Using this technique, identify the reagents that you would need in order to prepare rheosmin via a crossed aldol reaction. Rheosmin is isolated from raspberries and is often used in perfume formulations for its pleasant odor. Hint: The presence of a phenolic proton will be problematic during an aldol reaction. (Can you explain why?) Consider using a protecting group (Section 13.7). Rheosmin HO O

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QUESTION:

The product of an aldol condensation is an a,b-unsaturated ketone which is capable of undergoing hydrogenation to yield a saturated ketone. Using this technique, identify the reagents that you would need in order to prepare rheosmin via a crossed aldol reaction. Rheosmin is isolated from raspberries and is often used in perfume formulations for its pleasant odor. Hint: The presence of a phenolic proton will be problematic during an aldol reaction. (Can you explain why?) Consider using a protecting group (Section 13.7). Rheosmin HO O

ANSWER:

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The product of an aldol condensation can undergo hydrogenation to yield a saturated ketone. This is standard chemistry that we have used continually throughout the text. We’re asked to use this approach to prepare the molecule named rheosim via a crossed aldol reaction. Recall that in a crossed aldol reaction, we maintain control over which carbonyl becomes the nucleophilic enol or enolate and which carbonyl remains unchanged, serving as the electrophilic target.

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