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Propose a plausible mechanism for the following

Chapter 9, Problem 9.9

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QUESTION:

Propose a plausible mechanism for the following transformation, which was used as the key step in the formation of the natural product heliol (Org. Lett. 2012, 14, 2929–2931):

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QUESTION:

Propose a plausible mechanism for the following transformation, which was used as the key step in the formation of the natural product heliol (Org. Lett. 2012, 14, 2929–2931):

ANSWER:

Step 1 of 5

Mechanism for the formation of the tricyclic product :

 

 

The first step of the mechanism involves the protonation of the more basic tertiary alcohol to give an activated leaving group. 

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