Synthesis of the N-Acyl Amycolose Moiety of Amycolamicin and Its Methyl Glycosides
Synthesis of the N-Acyl Amycolose Moiety of Amycolamicin and Its Methyl Glycosides
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DOI：
10.1021/acs.joc.9b00650
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发表时间：
2019-06-07
影响因子：
3.6
通讯作者：
Kuwahara, Shigefumi
中科院分区：
文献类型：
--
作者：
Meguro, Yasuhiro;Ogura, Yusuke;Kuwahara, Shigefumi
由土壤放线菌产生的广谱抗菌天然产物阿米卡米星中的N-酰基淀粉糖部分及其两个异构体甲基糖苷，通过利用对甲氧基苄氧基取代的乙烯基锂试剂与α，β-双烷氧基酮中间体的非对映选择性加成，提供相应的叔醇作为单一的非对映异构体，在已知的(R)-乳酸衍生物中经12步对映体选择性地合成。这三种糖衍生物被称为阿米可霉素的细胞毒性降解产物。
The N-acyl amycolose moiety incorporated in amycolamicin, a broad-spectrum antibacterial natural product produced by soil actinomycetes, and its two anomeric methyl glycosides have been synthesized enantioselectively each in 12 steps from a known methyl (R)-lactate derivative by exploiting a diastereoselective nucleophilic addition of a p-methoxybenzyloxy-substituted vinyllithium reagent to an alpha,beta-bisalkoxy ketone intermediate to provide the corresponding tertiary alcohol as a single diastereomer. The three sugar derivatives are known as cytotoxic degradation products of amycolamicin.