Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-L-lyxohexopyranose (Lemonose)
Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-L-lyxohexopyranose (Lemonose)
复制标题
DOI：
10.1055/s-0030-1259531
复制
发表时间：
2011-03-01
期刊：
影响因子：
2
通讯作者：
Zhu, Jieping
中科院分区：
文献类型：
--
作者：
Bernadat, Guillaume;George, Nicolas;Zhu, Jieping
L-柠檬糖是 (-)-柠檬霉素的糖苷部分，经过十步合成，D-苏氨酸的总产率为 18%。关键步骤是对 Weinreb 酰胺进行双高度非对映选择性格氏加成，以及在仲醇、叔醇和叔胺存在下对伯醇进行化学选择性氧化，直接生成乳醇。
L-Lemonose, the glycosidic part of (-)-lemonomycin, has been synthesized in ten steps with 18% overall yield from D-threonine. The key steps are a double, highly diastereoselective Grignard addition to a Weinreb amide and a chemoselective oxidation of a primary alcohol in the presence of a secondary alcohol, a tertiary alcohol and a tertiary amine, leading directly to the lactol.