46 ビシクロ[3.2.2]ノナン類の転位反応を活用した縮環骨格形成 : (±)-セスキカレン,(±)-ピングイソン,(±)-ウィドロールおよび(±)-プチロカウリンの全合成

概要

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The methods examined for the construction of [m-n] fused-ring skeletones are the photochemical [3,3]-sigmatropic rearrangement of bicyclo[3.2.2]nona-3,6-dien-2-ones into endo-7-bicyclo[4.1.0]hept-2-enyl ketenes (method-1) and the photochemical [1,3]-acyl migration of bicyclo[3.2.2]non-6-en-2-ones into bicyclo[4.3.0]non-4-en-7-ones (method-2). The pinacol-type rearrangement of 1-methoxybicyclo[3.2.2]non-6-en-2-ols (method-3) has been developed in order to establish the formal bridgehead-substitution and/or to interchange the saturated bridges each other. The natural products, synthesized based on these methods, are the [3-6] fused-ring hydrocarbon (±)-sesquicarene (method-1), the [5-6] fused-ring furano-sesquiterpene (±)-pinguisone (method-2), the [6-7] fused-ring sesquiterpene (±)-widdrol (method-3), and the antitumor antibiotic (±)-ptilocaulin (methods-3 and -2).
天然有機化合物討論会の論文
1986-09-09