Studies toward a marine toxin immunogen: Enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine
Studies toward a marine toxin immunogen: Enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine
复制标题
DOI：
10.1021/ol051840r
复制
发表时间：
2005-11-10
期刊：
影响因子：
5.2
通讯作者：
Romo, D
中科院分区：
文献类型：
--
作者：
Kong, K;Moussa, Z;Romo, D
利用Evans的铜-双恶唑啉配合物催化的不对称Diels-Alder反应构建了高度官能化的螺内酰胺，这是我们计划合成海洋毒素Gynodimine的关键中间体。额外的转化，包括温和的N-甲苯磺基去保护，提供了一个酮基螺环亚胺部分，建议的药效团的绞股蓝。因此，所制备的酮是一种潜在的有用的偶联中间体，为最终监测绞股蓝及其同系物提供免疫原。
An enantioselective Diels-Alder reaction catalyzed by an Evans' copper-bis(oxazoline) complex was utilized to construct a highly functionalized spirolactam, a key intermediate in our projected total synthesis of the marine toxin, gymnodimine. Additional transformations, including a mild N-tosyl group deprotection, afforded a keto spirocyclic imine moiety, the proposed pharmacophore of gymnodimine. Thus, the prepared ketone is a potentially useful intermediate for conjugation to provide an immunogen for eventual monitoring of gymnodimine and congeners.