Download PDF
Synfacts 2023; 19(02): 0117
DOI: 10.1055/s-0042-1753247
Synthesis of Natural Products

Total Synthesis of (+)-Monensin

Contributor(s):
Erick M. Carreira
,
Moritz E. Hansen
Fukuyama T, Akasaka K, Karanewsky DS, Wang CL. J, Schmid G, Kishi Y. * Harvard University, Cambridge, USA
Synthetic Studies on Polyether Antibiotics. 6. Total Synthesis of Monensin. 3. Stereocontrolled Total Synthesis of Monensin.

J. Am. Chem. Soc. 1979;
101: 262-263
CrossrefSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

(+)-monensin - polyether antibiotics - Brown hydroboration - Prilezhaev reaction - Wittig olefination - aldol addition

Significance

In their landmark synthesis of the stereochemically complex polyether antibiotic ­(+)-monensin, published in three consecutive commu­nications, Kishi and co-workers showcase elegant use of allylic strain as stereocontrol ­element.


#

Comment

Coupling of left and right half E and L was, after considerable experimentation, achieved by aldol addition using a magnesium amide base. Deprotection of benzyl ether M, ketal equilibration, and saponification gave the (+)-monensin sodium salt.


#
#

Publication History

Article published online:
17 January 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints