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Synfacts 2022; 18(10): 1153
DOI: 10.1055/s-0041-1738591
DOI: 10.1055/s-0041-1738591
Innovative Drug Discovery and Development
A Convergent Synthesis of (+)-Ikarugamycin
Paquette LA,
*,
Macdonald D,
Anderson LG.
The Ohio State University, Columbus, USA
Total Synthesis of (+)-Ikarugamycin. 2. Elaboration of the Macrocyclic Lactam and Tetramic Acid Substructures and Complete Assembly of the Antibiotic.
J. Am. Chem. Soc. 1990;
112: 9292-9299
DOI: 10.1021/ja00181a035.
Total Synthesis of (+)-Ikarugamycin. 2. Elaboration of the Macrocyclic Lactam and Tetramic Acid Substructures and Complete Assembly of the Antibiotic.
J. Am. Chem. Soc. 1990;
112: 9292-9299
DOI: 10.1021/ja00181a035.
Significance
Ikarugamycin (IKA) is an antibiotic that is isolated from Streptomyces phaeochromogenes. IKA inhibits clathrin-mediated endocytosis and has been proposed as a tool compound to probe endocytic trafficking in cells.
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Comment
Paquette and co-workers used a convergent method to assemble (+)-ikarugamycin. A kinetic resolution via a 1,4-addition of vinylmagnesium bromide to diastereomeric aldimines was key to their success. The macrolactamization was achieved through trapping a transiently generated ketene intermediate.
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Publication History
Article published online:
20 September 2022
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