Catalytic Asymmetric Total Synthesis of (+)-Caprazol
Organic Letters2014Vol. 16(12), pp. 3364–3367
Citations Over TimeTop 10% of 2014 papers
Purushothaman Gopinath, Lu Wang, Hikaru Abe, G. Ravi, Takashi Masuda, Takumi Watanabe, Masakatsu Shibasaki
Abstract
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 β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-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.
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