title: Synthesis of glycocinnasperimicin D.
abstract: The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the alpha-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.
authors: School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors: Taihei
authors: T
authors: Nishiyama
authors: Yoshifumi
authors: Y
authors: Kusumoto
authors: Ken
authors: K
authors: Okumura
authors: Kanako
authors: K
authors: Hara
authors: Shohei
authors: S
authors: Kusaba
authors: Keiko
authors: K
authors: Hirata
authors: Yukihiro
authors: Y
authors: Kamiya
authors: Minoru
authors: M
authors: Isobe
authors: Keiji
authors: K
authors: Nakano
authors: Hiyoshizo
authors: H
authors: Kotsuki
authors: Yoshiyasu
authors: Y
authors: Ichikawa
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D015394:Molecular Structure; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; C046892:glycocinnasperimicin D; D013095:Spermidine