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-alle1) and L- Pro9 r...

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Published inTetrahedron Vol. 52; no. 12; pp. 4327 - 4346
Main Authors Kurome, Toru, Inami, Kaoru, Inoue, Tetsuya, Ikai, Katsushige, Takesako, Kazutoh, Kato, Ikunoshin, Shiba, Tetsuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.03.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RACEMIZATION
PEPTIDE-SYNTHESIS
ACIDS
CYCLOSPORINE
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Summary: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-alle1) 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. A total synthesis of an antifungal cyclic depsipeptide aureobasidin A was first achieved mainly using PyBroP as a coupling reagent. The synthetic cyclized product is completely identical with the natural antibiotic in all respects.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00132-9