Total synthesis and antimalarial activity of symplostatin 4.
The first total synthesis of symplostatin 4, a marine cyanobacterium-derived natural product, is described. Notable features of the route include the efficient preparation of three key fragments and final assembly to the natural product via sequential imide and amide couplings. Symplostatin 4 was also demonstrated to possess significant antimalarial activity (ED(50) of 74 nM against Plasmodium falciparum, strain 3D7).
School of Chemistry, The University of Sydney, NSW 2006, Australia.
Trent
T
Conroy
Jin T
JT
Guo
Nicholas H
NH
Hunt
Richard J
RJ
Payne
D000962:Antimalarials / Q000138:chemical synthesis*; D023181:Antimicrobial Cationic Peptides; D001688:Biological Products / Q000138:chemical synthesis; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*
D000962:Antimalarials; D023181:Antimicrobial Cationic Peptides; D001688:Biological Products; D010455:Peptides; C534687:gallinamide A