Catalytic Asymmetric Total Synthesis of (+)-Caprazol

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• 作者：Purushothaman Gopinath ; Lu Wang ; Hikaru Abe ; Gandamala Ravi ; Takashi Masuda ; Takumi Watanabe ; Masakatsu Shibasaki
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：June 20, 2014
• 年：2014
• 卷：16
• 期：12
• 页码：3364-3367
• 全文大小：343K
• 年卷期：v.16,no.12(June 20, 2014)
• ISSN：1523-7052

文摘

Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C鈥揅 bond forming reactions as key transformations. The stereochemistries of the 尾-hydroxy-伪-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the 尾-hydroxy-伪-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.