Selective photochemical cleavage of an α-ketoamide in a highly functionalised macrolide ascomycin

(6- S)-Methoxyascomycin and its protected derivatives undergo cleavage of the pipecolic acid amide bond upon irradiation in MeOH. The potential of this reaction towards a semi-synthetic strategy is explored. A novel photochemical amide cleavage reaction of (6 S)-methoxyascomycin opening a pathway fo...

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Bibliographic Details
Published in:Tetrahedron letters 2004-03, Vol.45 (12), p.2527-2530
Main Authors: Bulusu, Murty A.R.C., Waldstätten, Peter, Tricotett, Thomas, Schulz, Gerhard
Format: Article
Language:English
Subjects:
Photochemical amide cleavage
Phototransformation
Zwitterion
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Summary:(6- S)-Methoxyascomycin and its protected derivatives undergo cleavage of the pipecolic acid amide bond upon irradiation in MeOH. The potential of this reaction towards a semi-synthetic strategy is explored. A novel photochemical amide cleavage reaction of (6 S)-methoxyascomycin opening a pathway for the selective cleavage of the pipecolic acid, is described. The scope of this reaction with several analogues carrying suitable protecting groups is examined.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.02.014