title: A new route to platencin via decarboxylative radical cyclization.
abstract: A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)4 in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. yoshimit@phs.osaka-u.ac.jp.
authors.forename: Gamal A I
authors.initials: GA
authors.lastname: Moustafa
authors.forename: Yuki
authors.initials: Y
authors.lastname: Saku
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Aoyama
authors.forename: Takehiko
authors.initials: T
authors.lastname: Yoshimitsu
mesh_terms: D000627:Aminophenols / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003653:Decarboxylation; D004146:Dioxanes / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism
chemical_list: D000627:Aminophenols; D000900:Anti-Bacterial Agents; D001688:Biological Products; D004146:Dioxanes; D005609:Free Radicals; D009942:Organometallic Compounds; D011083:Polycyclic Compounds; D011725:Pyridines; C025223:1,4-dioxane; C023666:pyridine; C520340:platencin