What is the function of methylguaiacol (8) in the synthesis of (-)-halenaquinone?
Label:chem
Topic
Methylguaiacol (8) is used in the oxidative ketalization step of the synthesis.
Answer
Methylguaiacol (8) acts as a dienophile in the oxidative ketalization reaction with the dienol precursor (7). This reaction forms a mixture of adducts (9 and 10), which are then converted to the desired naphthofuranone (9) via the Cope rearrangement.
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