Putting Good Ideas to Use

Step 1. Ni(0)-catalyzed coupling Step 2. loss of protecting group R  

SCHEME 3. Conditions that the phenol protecting group R must withstand 

Once we knew how to differentiate methoxy groups in 4, all the pieces fell into place, at least on paper. Major decisions still had to be made, however. For example, protecting group chemistry the newly generated phenol 5, an acid, would not be tolerated during the eventual 

SCHEME 4. Selective demethylation of readily available aldehyde 4 

SCHEME 5. Retrosynthesis of coupling partner vinyl alane 6. 

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