- Novel skeleton transformation reaction of α-pyrone derivatives to spirobicyclo[3.1.0]hexane derivatives using dimethylsulfoxonium methylide.
Novel skeleton transformation reaction of α-pyrone derivatives to spirobicyclo[3.1.0]hexane derivatives using dimethylsulfoxonium methylide.
Organic letters (2012-11-21)
Takuya Miura, Navnath Dnyanoba Yadav, Hiroki Iwasaki, Minoru Ozeki, Naoto Kojima, Masayuki Yamashita
PMID23163935
ABSTRACT
By applying a skeleton transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of this reaction, it was confirmed that it is possible to apply this reaction to not only ring-fused α-pyrone derivatives but also alkyl-chain-substituted α-pyrone derivatives in moderate to good yields.
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