Photochemical cycloaddition reactions of .ALPHA.,.BETA.-unsaturated lactones with olefins, and application to synthesis of natural products.

概要

論文の詳細を見る
The photochemical cycloaddition reactions of five- and six-membered α,β-unsaturated lactone derivatives with unsaturated substrates (ethylene, acetylene, 1,1-dimethoxyethylene <I>etc.</I>) have been studied. The parent α,β-unsaturated lactone (γ-crotonolactone) and the β-,γ-, or δ-alkyl substituted derivatives add to ethylene and acetylene in the acetone solutions and to 1,1-dimethoxyethylene in the benzene solutions in so good yields as to utilize them practically for synthesis. α-Phenyl-γ-crotonolactone and β-phenyl-γ-crotonolactone also add to ethylene and acetylene, whereas, α-methyl, β-hydroxy, and β-methoxy derivatives do not. As the synthetic applications of the reactions, the synthesis of (±)-grandisol has been achieved, and the synthetic approach to (±)-canadensolide has also been described.
公益社団法人日本化学会の論文