連続的多重マイケル反応によるアヌレーション
-テルペノイド合成の一断面-
1992 年 50 巻 8 号 p. 713-725
詳細
1992 年 50 巻 8 号 p. 713-725
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 [4.4.0.01.5] decane or tricyclo [3.2.1.02.7] 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 [5.3.1.03.8] undecane derivatives. These successive multifold Michael reactions have enabled the synthetic studies of ε-cadinene, khusitone, khusilal, isoeremolactone, ishwarane, and seychellene.
