連続的多重マイケル反応によるアヌレ-ション--テルペノイド合成の一断面
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概要
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The kinetic enolates or trimethylsilyl enol ethers of 1-acetylcyclohexene undergo successive double Michael reactions with α, β-unsaturated carbonyl compounds to give substituted decalones. The kinetic enolates of cyclohexenone provide bicyclo [2.2.2] octane derivatives via double Michael reaction. These double Michael reactions have been extended to bicycloannulation leading to tricyclo [4.4.0.0<SUP>1.5</SUP>] decane or tricyclo [3.2.1.0<SUP>2.7</SUP>] octane compounds by employing α-bromo-α, β-unsaturated esters with cyclohexenone or 1-acetylcyclohexene, respectively. Divinylketone and the trimethylsilyl enol ethers of cyclohexenone undergo Lewis acid assisted triple Michael reactions yielding tricyclo [5.3.1.0<SUP>3.8</SUP>] undecane derivatives. These successive multifold Michael reactions have enabled the synthetic studies of ε-cadinene, khusitone, khusilal, isoeremolactone, ishwarane, and seychellene.
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