Total synthesis of cristatic acid.
The first total synthesis of cristatic acid 1, an antibiotic endowed with considerable activity against Gram-positive bacteria, hemolytic properties, and significant cytotoxicity, is described. Key to success are the formation of its 2,4-disubstituted furan moiety via a palladium-catalyzed alkylation of vinylepoxide 10 derived from sulfonium salt 8 and the use of SEM ethers as the protecting groups for the phenolic OH functions.
Fürstner
A
A
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany. fuerstner@mpi-muelheim.mpg.de
Gastner
T
T
D000363:Agaricales; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D012459:Salicylates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D005663:Furans; D007202:Indicators and Reagents; D012459:Salicylates; C413203:cristatic acid