title: 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.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Shuto
authors.forename: S
authors.initials: S
authors.lastname: Ichikawa
authors.forename: A
authors.initials: A
authors.lastname: Matsuda
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007454:Iodides; D011684:Purine Nucleosides; D012493:Samarium; C013551:herbicidins; C409809:samarium diiodide