title: Catalytic asymmetric total synthesis of (+)-caprazol.
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.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN), Tokyo , 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Purushothaman
authors.initials: P
authors.lastname: Gopinath
authors.forename: Lu
authors.initials: L
authors.lastname: Wang
authors.forename: Hikaru
authors.initials: H
authors.lastname: Abe
authors.forename: Gandamala
authors.initials: G
authors.lastname: Ravi
authors.forename: Takashi
authors.initials: T
authors.lastname: Masuda
authors.forename: Takumi
authors.initials: T
authors.lastname: Watanabe
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D000900:Anti-Bacterial Agents; D001381:Azepines; D009705:Nucleosides; C512216:caprazol; C116609:3-hydroxybutanal; D014529:Uridine