• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>European journal of organic chemistry >Total synthesis of (+)-hyacinthacine A_1, (+)-7a-epi- hyacinthacine A_1, (6R)-6-hydroxyhyacinthacine A1 and (6S)-6-hydroxy-7a-epi-hyacinthacine A_1
【24h】

Total synthesis of (+)-hyacinthacine A_1, (+)-7a-epi- hyacinthacine A_1, (6R)-6-hydroxyhyacinthacine A1 and (6S)-6-hydroxy-7a-epi-hyacinthacine A_1

机译：（+）-扁豆碱A_1，（+）-7a-表扁豆碱A_1，（6R）-6-羟基扁豆碱A1和（6S）-6-羟基-7a-表扁豆碱A_1的全合成

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

The total synthesis of natural (+)-hyacinthacine A_1 (6), (+)-7a-epi-hyacinthacine A1 (7) and their 6-hydroxy analogues 21 and 16 was achieved using a nitrone cycloaddition strategy with D-ribose-derived cyclic nitrone 8 as the dipole and tert-butyl acrylate as the dipolarophile. After separation of the adducts, reductive cleavage of the N-O bond followed by lactam reduction and deprotection afforded the two non-natural hydroxy analogues in excellent yields. The synthesis of (+)-hyacinthacine A_1 (6) and of (+)-7a-epi-hyacinthacine A_1 (7), which required deoxygenation at C(6), was accomplished by DIBAL-H reduction of mesylate derivatives of the pyrrolizidinols 20 and 15, respectively. Evaluation of the synthesized compounds against a panel of 12 commercially available glycosidases showed that hyacinthacine A_1 (6) and its (6R)-hydroxy analogue 21 are good inhibitors of amyloglucosidase; the non-natural compound 21 is also a strong inhibitor of β-glucosidase, while 6 showed only moderate inhibition. The non-natural (+)-7a-epi-hyacinthacine A1 (7) is a moderate inhibitor of amyloglucosidase and α-L-fucosidase; the presence of the (6S)-hydroxy group in 16 led to diminished activity.
机译：天然（+）-扁豆碱A_1（6），（+）-7a-表-扁豆碱A1（7）及其6-羟基类似物21和16的总合成是通过使用D-核糖衍生的硝酮环加成策略实现的环状硝酮8为偶极子，丙烯酸叔丁酯为偶极子。在分离加合物之后，N-O键的还原性切割，然后内酰胺还原和脱保护，以优异的产率提供了两种非天然羟基类似物。 （+）-hyacinthacine A_1（6）和（+）-7a-epi-hyacinthacine A_1（7）的合成需要在C（6）上进行脱氧，其方法是通过DIBAL-H还原吡咯烷二醇的甲磺酸盐衍生物来完成。 20和15。对合成的化合物针对一组12种市售糖苷酶的评估显示，风信氨酸A_1（6）及其（6R）-羟基类似物21是淀粉葡糖苷酶的良好抑制剂;非天然化合物21还是β-葡萄糖苷酶的强抑制剂，而6则仅显示中度抑制作用。非天然（+）-7a-表-葡萄球菌素A1（7）是淀粉葡糖苷酶和α-L-岩藻糖苷酶的中度抑制剂。 （16S）-羟基的存在会导致活性降低。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号