The first synthesis of herbicidin B, a tricyclic-sugar adenine nucleoside antibiotic, using samarium diiodide-promoted aldol-type C-glycosidation reaction as a key-step.
A first total synthesis of the nucleoside antibiotic herbicidin B (1) was achieved in which a novel aldol-type C-glycosidation reaction promoted by samarium diiodide (SmI2) was used as a key step. Construction of the desired stereochemistry of the tricyclic-sugar moiety was successfully achieved by conformational restriction strategy based on repulsion between adjacent bulky protecting groups on the pyranose ring.
Shuto
S
S
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Ichikawa
S
S
Matsuda
A
A
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D007202:Indicators and Reagents; D007454:Iodides; D008968:Molecular Conformation; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007454:Iodides; D011684:Purine Nucleosides; D012493:Samarium; C013551:herbicidins; C409809:samarium diiodide