The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. Attempted Pummerer reaction of a furan sulfoxide derivative produced four interesting furan derivatives. Base promoted annulation between methyl 2-(phenylsulfinylmethyl)-3-furoate and 2-cyclohexenone proceeded to give dihydro naphtho[2,3-b]furanone derivative in a regiospecific manner.
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