新型五元环状过氧化物衍生物的合成方法

Novel approach to synthesis of 1,2 dioxolanes

环状过氧化物作为一类具有生物活性的天然产物的结构单位，其合成方法的研究对于这类天然产物的合成具有重要的指导作用。在醋酸锰（Ⅲ）与氧气的存在下， 苯乙炔与２， ４－戊二酮反应生成４－乙酰基－３－甲基－５－苯甲酰基－１，２－二氧五环－３－醇（１４％ ），２－乙酰基－３－苯甲酰基环氧丙烷（２６％ ）与２－乙酰基－３－甲基－４－苯基呋喃（５％ ）； ４－甲基苯乙炔在相同条件下反应得到相应的１， ２－二氧五环衍生物，产率约为１２％ ；

Synthetic studies on cyclic peroxide which constitutes active structure unit in some natural substances are of great importance to the total synthesis. The reaction of phenylethyne with 2,4 pentanedione in the presence of manganese(Ⅲ) acetate and oxygen gave 4 acetyl 5 benzoyl 3 methyl 1,2 dioxolane 3 ol (14%), 2 acetyl 3 benzoyloxirane (26%), and 2 acetyl 3 methyl 4 phenylfuran (5%). The reaction of 4 substituted phenylethynes was also examined and gave the corresponding dioxolanes in ca. 12% yields. The structure of the synthesized compounds was determined by 1H NMR, 13 C NMR, IR, as well as elemental analysis. The radical reaction mechanism was discussed.