154561-18-9

Upstream product

• 37553-65-4 Boc-N-Me-Phe-OH 
• 70-11-1 α-bromoacetophenone 
• 110345-80-7 1-(tert-butyl) 2-(2-oxo-2-phenylethyl) (S)-pyrrolidine-1,2-dicarboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 

Downstream Products

• 154524-89-7 C₆₁H₈₆N₆O₁₃ 
• 127785-64-2 aureobasidin A 
• 154524-87-5 Boc-L-MeVal-L-Phe-L-MePhe-L-Pro-OPac 
• 154524-86-4 Boc-L-Phe-L-MePhe-L-Pro-OPac 

Relevant academic research and scientific papers

Total synthesis of an antifungal cyclic depsipeptide aureobasidin A

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.

Total Synthesis of Aureobasidin A, an Antifungal Cyclic Depsipeptide

A total synthesis of an antifungal cyclic depsipeptide aureobasidin A was first achieved mainly using PyBroP as a coupling reagent.The synthetic cyclized product was completely identical with the natural antibiotic in all respects.Some unexpected reactions due to N-methylamino acid were also described.