A new route to platencin via decarboxylative radical cyclization

• Published in: Chemical communications (Cambridge, England) Vol. 50; no. 99; pp. 15706 - 15709
• Main Authors: Moustafa, Gamal A. I., Saku, Yuki, Aoyama, Hiroshi, Yoshimitsu, Takehiko
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 25.12.2014
• Subjects: Aminophenols - chemical synthesis; Aminophenols - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Antibiotics; Biological Products - chemical synthesis; Biological Products - chemistry; Bonding; Chemistry; Chemistry, Multidisciplinary; Crystallography, X-Ray; Cyclization; Decarboxylation; Dioxanes - chemistry; Esters; Free Radicals - chemistry; Molecular Conformation; Natural products; Organometallic Compounds - chemistry; Physical Sciences; Polycyclic Compounds - chemical synthesis; Polycyclic Compounds - chemistry; Pyridines; Pyridines - chemistry; Radicals; Refluxing; Science & Technology; Streptomyces - chemistry; Streptomyces - metabolism; OXIDATION; FORMAL TOTAL-SYNTHESIS; PLATENSIMYCIN; INHIBITOR; ALKENYLATION; DISCOVERY; CARBOXYLIC-ACIDS; (+/-)-PLATENCIN; FABF
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c4cc07316a

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.