8,8 -二取代 -2 -氧杂双环 [3 .2 .1]-辛 -3 -酮类化合物的合成

SYNTHESIS OF 8,8 DISUBSTITUTED-2-OXABICYCLO [3.2.1]-OCTAN-3-ONE

以 2 -甲基 -1 ,3 -环戊二酮为原料 ,经过烷基化 ,Wittig-Horner反应 ,催化氢化 ,硼氢化钠还原 ,酸催化下分子内酯交换反应 ,合成了相应的双环内酯 ,共十六个化合物 ,其中十二个未见报道 .通过 IR,1 NHMR,元素分析或质谱分析确定了化合物的结构 .通过1 NHMR确定了 6个顺反异构体的构型 .

Using 2 methyl cyclopentane 1,3 dione as start material, the title bicyclolactone was synthesized via alkylation, Wittig Horner reaction, catalytic hydrogenation, sodium borohydride reduction and acid catalyzed intramolecular transesterification. Total sixteen compounds wre synthesized, twelve of which haven't been reported. The structures of all compounds were determined by IR, 1HNMR, element analysis or mass analysis. The configuration of six geometric isomers were determined by 1HNMR.