Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X

Chapter 23, Problem 23.28

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Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the fi rst step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o-lantern, a poisonous, saffron-colored mushroom. What is the structure of X? O HO OH CH2OH illudin-S C CH3 CH2CO2Et O NaOEt several steps (2 equiv) Br Br + X

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