Total synthesis of (+)-FR-900493 and establishment of its absolute stereochemistry
Total synthesis of (+)-FR-900493 and establishment of its absolute stereochemistry
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DOI：
10.1016/j.tet.2007.01.055
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发表时间：
2007-03-26
期刊：
影响因子：
2.1
通讯作者：
Matsuda, Akira
中科院分区：
文献类型：
--
作者：
Hirano, Shinpei;Ichikawa, Satoshi;Matsuda, Akira
报道了具有6 ′-N-烷基-5 ′-O-氨基核糖基甘氨酰尿苷结构的核苷类抗菌抗生素（+）-FR-900493的首次全合成，并建立了其相对和绝对立体化学。该方法的关键要素包括氨基核糖部分的早期引入和氨基在6 '-位的两个连续还原烷基化。该合成策略可应用于相关核苷类抗生素的合成，如抗菌活性更强的核苷类抗生素，胞壁霉素。(c)2007爱思唯尔有限公司保留所有权利。
The first total synthesis of (+)-FR-900493, an antibacterial nucleoside antibiotic possessing a 6'-N-alkyl-5'-O-aminoribosylglycyluridine structure, is described, and its relative and absolute stereochemistries were established. Key elements of the approach include the early-stage introduction of the aminoribose moiety and two sequential reductive alkylations of an amino group at the 6'-position. This synthetic strategy could be applicable to the synthesis of related nucleoside antibiotics, such as the more potent antibacterial nucleoside antibiotics, muraymycins. (c) 2007 Elsevier Ltd. All rights reserved.