Catalytic Asymmetric Total Synthesis of (+)-Caprazol
Catalytic Asymmetric Total Synthesis of (+)-Caprazol
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DOI：
10.1021/ol501397b
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发表时间：
2014-06-20
期刊：
影响因子：
5.2
通讯作者：
Shibasaki, Masakatsu
中科院分区：
文献类型：
--
作者：
Gopinath, Purushothaman;Wang, Lu;Shibasaki, Masakatsu
以两个立体选择性的C-C键形成反应为关键反应，催化不对称全合成了脂质核苷类抗生素Caprazol。尿苷部分和二氮杂环庚烷酮部分的交界处的β-羟基-α-氨基酯部分的立体化学，以及嵌入在二氮杂环庚烷酮系统中的β-羟基-α-氨基酸部分的立体化学，分别使用非对映选择性异氰酸酯醛醇缩合反应（dr = 88：12）和由Nd/Na-手性酰胺配体催化的对映选择性反硝基醛醇缩合反应（dr = 12：1，95%ee）构建。
Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the beta-hydroxy-alpha-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the beta-hydroxy-alpha-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.