154561-18-9Relevant articles and documents
Total synthesis of an antifungal cyclic depsipeptide aureobasidin A
Kurome, Toru,Inami, Kaoru,Inoue, Tetsuya,Ikai, Katsushige,Takesako, Kazutoh,Kato, Ikunoshin,Shiba, Tetsuo
, p. 4327 - 4346 (2007/10/03)
The first total synthesis of antifungal cyclic depsipeptide aureobasidin A is described. The synthesis was achieved mainly using bromotris(pyrrolidino)phosphonium hexafluorophosphate (PyBroP) as a coupling reagent. Peptide cyclization was carried out between L-allo-isoleucine (L-aIle1) and L-Pro9 residues in the linear nonapeptide at the final step of the synthesis. Synthesized aureobasidin A was completely identical with the natural antibiotic with respect to antifungal activity and physicochemical properties. Unusual reactions due to N-methylamino acid, an oxazoline-mediated reaction and an N, O-acyl migration, are also described.