Synthesis of Compound E
  • The first 2 steps create the core carbon chain using alkyne anions
  • Then HBr is added to the triple bond to create 2 anti-addition products
  • A methyl group replaces bromine using Grinard.
  • NBS causes radical  substitution at allylic position, and bromine's high selectivity makes secondary substitution favorable (p. 337).  This creates 2 different major products.
  • Finally, -OH subsitutes bromine.

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