Do electrons get motion sickness ?

Chemistry Level 3

Pericyclic reactions have been used to generate cyclic structures in organic synthesis. This question explores one such reaction :

The product X has a three-fold rotational symmetry axis and is generated using the reaction given below:

With a basic understanding of this reaction, we move to a synthesis proposed by Chinese researchers in 2013 for an interesting alkaloid, M , isolated from the plants of the Daphiphyllum genus which is used in Chinese medicine to ease nausea. This reaction scheme is shown below:

Note that the stereocenter in B is enantiomerically isolated as an S isomer using PLE.

If α \alpha denotes the number of rings in X and β \beta denotes the number of rings in M ,

Calculate the value of α + β \alpha + \beta

BONUS

  • Deduce structures of X and A - M
  • Provide a mechanism for the reaction of B to C
  • Provide a brief explanation of the underlying reaction in these two synthesis

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The answer is 9.

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