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Q.30-16

Question


Coronafacic acid, a bacterial toxin, was synthesized using a key step that involves three sequential pericyclic reactions. Identify them, and propose a mechanism for the overall transformation. How would you complete the synthesis?[pk1] 

 [pk1]Size should be 12 not 11.



Step-by-Step Solution

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Answer
  1. Ring opening of 6 membered ring
  2. Opening of 4 membered ring
  3. 4+2 cyclic addition.
  4. Hydrolysis
1Opening of 6 membered ring


First step is the ring opening of 6 membered ring.



2Opening of 4 membered ring


Second step is opening of 4 membered ring.



34+2 cyclic addition


Third step is 4+2 cyclic addition.



4Hydrolysis to produce Coronafacic acid


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