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The following sequence of reactions was performed during a
Chapter 8, Problem 8.91(choose chapter or problem)
The following sequence of reactions was performed during a synthesis of (+)-coronafacic acid, a key component in the plant toxin coronatine (J. Org. Chem. 2009, 74, 2433-2437). Predict the product of this reaction sequence and justify the regiochemical outcome of the second reaction.
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QUESTION:
The following sequence of reactions was performed during a synthesis of (+)-coronafacic acid, a key component in the plant toxin coronatine (J. Org. Chem. 2009, 74, 2433-2437). Predict the product of this reaction sequence and justify the regiochemical outcome of the second reaction.
ANSWER:Step 1 of 3
In this step of the reaction, the hydrogen which is directly bonded with the oxygen \((\mathrm{OH})\) is more acidic and abstracted by the base pyridine. This hydrogen is substituted by the tosyl group. The tosylate ion \(\text { (OTs) }\) is a good leaving group which is eliminated in the below second step of this reaction
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