γ-取代α,β-丁烯酸内酯的固相有机合成  

Solid-Phase Organic Synthesis of γ-Substituted α,β-Unsaturated γ-Butyrolactones

作　　者：刘晓玲[1] 康宜强[1] 王幸聪[1] 宋才生[1] 

机构地区：[1]江西师范大学化学学院,江西南昌330027

出　　处：《江西师范大学学报（自然科学版）》2003年第3期261-264,共4页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：江西省自然科学基金资助课题(001109)

摘　　要：以1%交联的聚苯乙烯为载体制备了新型的聚苯乙烯负载的α-硒基乙酸试剂.该试剂于0℃经二异丙基胺基锂(LDA)作用形成相应的α-碳负离子,与外消旋化的环氧化物或含光学活性的氧化苯乙烯反应,再经酸化、热环化得到聚苯乙烯负载α-硒基丁内酯;常温下将该负载型的α-硒基丁内酯用过量的30%双氧水处理制得相应的γ-取代α,β-丁烯酸内酯.该方法操作简便(过滤、洗涤),产率良好,粗产物不需进一步分离即具有较高的纯度.该法对含α,β-丁烯酸内酯的天然产物分子库的建立以及在药物筛选中均有潜在的应用.A novel polystyrene-supported α-selenoacetic acid was prepared from 1% cross-linked polystyrene resin. Reaction of the dilithio derivative of polystyrene-supported α-selenoacetic acid with racemic epoxides or optically active styrene oxide, followed by acidified with glacial acetic acid and lactonization afforded polystyrene-supported γ-substituted α-selenobutyrolactones. Subsequent oxidation-elimination with excess of 30% hydrogen peroxide at room temperature formed γ-substituted α,β-unsaturated γ-butyrolactones in high yields and good puritites without further purification. This procedure provided a convenient, wild and high-yielding method for preparation of γ-substituted α,β-unsaturated γ-butyrolactones.

关 键 词：γ-取代α β-丁烯酸内酯 固相有机合成 聚苯乙烯 α-硒基乙酸试剂 环氧化物 双氧水 

分 类 号：O623.624[理学—有机化学] O621.3[理学—化学]