ASYMMETRIC-SYNTHESIS OF BUTENOLIDE AND BUTYROLACTONE DERIVATIVES
ASYMMETRIC-SYNTHESIS OF BUTENOLIDE AND BUTYROLACTONE DERIVATIVES
复制标题
DOI：
10.1016/0957-4166(94)80085-5
复制
发表时间：
1994-09-01
影响因子：
--
通讯作者：
SIRIT, A
中科院分区：
文献类型：
--
作者：
PELTER, A;WARD, RS;SIRIT, A
2-三甲基硅氧基呋喃和4-甲氧基-2-三甲基硅氧基呋喃分别以丁烯内酯和四硝酸甲酯为原料，在Lewis酸存在下与一系列高手性原酯和恶唑烷衍生物反应，得到高手性2(5H)-呋喃酮衍生物。这些产品的结构已经用核磁共振波谱确定，并在可能的情况下，通过X射线分析确定。对这些不饱和内酯进行了共轭加成的初步实验，证明了它们作为天然产物合成底物的潜力。
2-Trimethylsiloxyfuran and 4-methoxy-2-trimethylsiloxyfuran, which are readily prepared from butenolide and methyl tetronate respectively, have been reacted with a series of homochiral ortho-esters and oxazolidine derivatives in the presence of Lewis acids to afford homochiral 2(5H)-furanone derivatives. The structures of these products have been determined using nmr spectroscopy and, where possible, by X-ray analysis. Preliminary experiments have been carried out involving conjugate addition to these unsaturated lactones, demonstrating their potential as substrates for natural product synthesis.