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Problem Set No. 3

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Modern Synthetic Methods Name:

D. Tyler McQuade

Problem Set No. 3

1. Wood et al. in their manuscript “Wharton-Fragmentation-Based Approach

to the Carbocyclic Core of the Phomoidrides” describe the following synthesis. Fill in the missing structures. An provide an arrow pushing mechanism for the transformation involving n-BuLi.

2. Draw the products for the following reactions a.

b.

3. Provide an arrow pushing mechanism for 2b and provide the name of this reaction.

4. Provide the missing intermediates (Org. Lett. 2012, 17, 4531–4533)

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