Synthesis of glycocinnasperimicin D.
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.
Nishiyama
Taihei
T
School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Kusumoto
Yoshifumi
Y
Okumura
Ken
K
Hara
Kanako
K
Kusaba
Shohei
S
Hirata
Keiko
K
Kamiya
Yukihiro
Y
Isobe
Minoru
M
Nakano
Keiji
K
Kotsuki
Hiyoshizo
H
Ichikawa
Yoshiyasu
Y
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
D000900:Anti-Bacterial Agents; C046892:glycocinnasperimicin D; D013095:Spermidine