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Chapter 24: Q.46. (page 962)

Question:What starting materials are needed to synthesize each compound using a Robinson annulation?

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

The Robinson annulation

The Robinson annulation involves the formation of a six membered cyclic ring from an α,β-unsaturated ketone and an enolate forming carbonyl compound. The steps in Robinson Annulation involve Michael addition followed by Aldol condensation.

An example is shown below:

Example of Robinson Annulation

02

Retrosynthetic analysis

a.

The retrosynthetic breakdown of the target molecule gives the following starting materials:

Starting materials of a

b.

The following starting materials are obtained upon retrosynthetic analysis:

Starting materials of b

c.

The following started materials undergo Robinson annulation to give the given product:

Starting materials of c

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Most popular questions from this chapter

Question: 2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasmine-like odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reaction between benzaldehyde (C6H5CHO)and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.

Question: Fill in the lettered reagents needed for each reaction.

Question:Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory fromo-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful syntheticanticoagulants.

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Question: Draw a stepwise mechanism for the following Robinson annulation. This reaction was a key step in a synthesis of the steroid cortisone by R. B. Woodward and co-workers at Harvard University in 1951.
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