14 α,β-不飽和ラクトンとオレフィンとの光環化付加反応を利用した二,三の天然物の合成研究

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Syntheses of (±)-grandisol, (±)-canadensolide, and (±)-fomannosin have been investigated by the use of photocycloaddition reactions of α,β-unsaturated lactones with olefins as the key steps. i) (±)-Grandisol has been stereoselectively synthesized from the photoadduct (3) between β-methyl-Δ^<α,β>-δ-lactone (2) and ethylene-(Fig. 1) ii) Bislactone (14), the precursor of (±)-canadensolide has been obtained from the photoadducts of γ-n-butyl-γ-crotonolactone with 1,1-dimethoxy ethylene. However, attempts to introduce exomethylene group have failed. -(Fig. 2) iii) Synthesis of deoxy dihydro fomannosin has been achieved starting from the photoadduct (19) of β-(4,4-dimethyl-2-oxocyclo-pentyl)-Δ^<α,β>-butenolide to ethylene. -(Fig. 3.4.5.)
天然有機化合物討論会の論文
1975-10-01