Five-membered ring annulation via thermal rearrangement of β-cyclopropyl α, β-unsaturated ketones. A formal total synthesis of the sesquiterpenoid (±)-zizaene

…, J Banville, CK Lau, I Nagakura

文献索引：Piers, Edward; Banville, Jacques; Lau, Cheuk Kun; Nagakura, Isao Canadian Journal of Chemistry, 1982 , vol. 60, p. 2965 - 2975

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被引用次数: 34

摘要

Treatment of the β-iodo enones 7-10 with lithium (phenylthio)(cyclopropyl) cuprate provided excellent yields of the corresponding β-cyclopropyl α, β-unsaturated ketones 11-14, respectively. When 3-isopropenyl-2-cyclohexen-1-one (16) was allowed to react with dimethyloxosulfonium methylide in dimethyl sulfoxide-tetrahydrofuran, 3-(1- methylcyclopropyl)-2-cyclohexen-1-one (17) was produced in 59% yield. Although ...