A Vanderwal favorite

The use of the compound W in organic synthesis for a variety of alkaloids has grown in recent years. Pyridine can be thought of as the dehydrated form of W . Interestingly W cannot be formed by the hydrolysis of Pyridine. Instead it requires another reaction, illustrated in the example below:

With this basic understanding of the formation of W and its derivatives, we now explore the chemistry that it contains within it. The below scheme illustrates an interesting reaction: (It is observed that Z contains an amide group and Ar denotes an aromatic group)

With this knowledge of the chemistry of W , we move on to a synthesis, proposed by American researchers, of a compound that can be considered as a core of an alkaloid isolated from Strychnos nux-vomica .

If $\alpha$ denotes the number of rings in E and $\beta$ denotes the number of rings in Z

Calculate the value of $\overline{\alpha\beta}$

BONUS

• Deduce structures of W - Z and A - E
• Provide a mechanism for the conversion of Y to Z and B to C

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