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Catalytic Asymmetric Total Synthesis of (+)-Caprazol

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journal contribution
posted on 20.06.2014, 00:00 by Purushothaman Gopinath, Lu Wang, Hikaru Abe, Gandamala Ravi, Takashi Masuda, Takumi Watanabe, Masakatsu Shibasaki
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.