Download PDF
Synfacts 2022; 18(10): 1153
DOI: 10.1055/s-0041-1738591
Innovative Drug Discovery and Development

A Convergent Synthesis of (+)-Ikarugamycin

Contributor(s):
Dirk Trauner
,
Matthew DiCairano
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
Search in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

kinetic resolution - Corey–Fuchs reaction - Boeckmann macrolactamization

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.


#

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.


#
#

Publication History

Article published online:
20 September 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints