Allylated monosaccharides as precursors in triple reductive amination strategies: synthesis of castanospermine and swainsonine.
Allylated monosaccharides as precursors in triple reductive amination strategies: synthesis of castanospermine and swainsonine.
复制标题
烯丙基化单糖作为三重还原胺化策略中的前体：栗精胺和苦马豆素的合成。
DOI：
10.1021/jo001447t
复制
发表时间：
2001
期刊：
影响因子：
--
通讯作者：
Mootoo,DR
中科院分区：
文献类型：
--
作者：
Zhao,H;Hans,S;Cheng,X;Mootoo,DR
三重还原胺化反应的合成复杂的吲哚里西啶框架的可行性，说明了应用到有效的糖苷酶抑制剂栗精胺和苦马豆素。目标化合物从已知的碳水化合物前体中获得，产率分别为23%和14%，经过9步和13步。烯丙基化单糖的碘醚化反应被证明是合成关键的三重还原胺化反应的三羰基前体的实用反应。
The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.