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Kato, Kosuke; Ikeuchi, Kazutada; Suzuki, Takahiro; Tanino, Keiji
Organic letters, 09/2022, Letnik: 24, Številka: 35Journal Article
A new method for constructing the bicyclo3.2.1octane skeleton was developed by the intramolecular alkylation of a nitrile-side-chain-containing cyclohexanone derivative. The cyclization precursors were prepared via the stereoselective bromination of the triisopropylsilyl enol ethers of 4-substituted cyclohexanones. Upon treatment with LiNEt2, the bromonitriles underwent a stereoselective intramolecular SN2 reaction to afford bicyclo3.2.1octane derivatives with a cyano group on the convex face. The total synthesis of 2-isocyanoallopupukeanane (6.5% yield) from methyl vinyl ketone was accomplished via a 17-step transformation.
