Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives
Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives
复制标题
DOI：
10.1002/asia.200600199
复制
发表时间：
2006-12-01
影响因子：
4.1
通讯作者：
Hayashi, Yujiro
中科院分区：
文献类型：
--
作者：
Matsuzawa, Masayoshi;Kakeya, Hideaki;Hayashi, Yujiro
以1，4-环己二酮单乙烯缩酮为关键步骤，通过催化不对称α-氨氧基化反应，完成了泛素活化酶（EI）抑制剂（+）-泛菲菊酯的不对称全合成。发现单体前体的仿生Diels-Alder反应在水中有效地进行。对（+）-panepophenanthrin的新衍生物的生物学性质的研究使我们能够开发新的细胞渗透性El抑制剂RKTS-80、RKTS-81和RKTS-82。
The asymmetric total synthesis of (+)-panepophenanthrin, an inhibitor of ubiquitin-activating enzyme (El), has been accomplished using catalytic asymmetric alpha aminoxylation of 1,4-cyclohexanedione monoethylene ketal as a key step, followed by several diastereoselective reactions. The biomimetic Diels-Alder reaction of a monomer precursor was found to proceed efficiently in water. The investigation of the biological properties of new derivatives of (+)-panepophenanthrin enabled us to develop new cell-permeable El inhibitors, RKTS-80, -81, and -82.