Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2023; 19(02): 0117
DOI: 10.1055/s-0042-1753247
DOI: 10.1055/s-0042-1753247
Synthesis of Natural Products
Total Synthesis of (+)-Monensin
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
DOI: 10.1021/ja00495a066.
Synthetic Studies on Polyether Antibiotics. 6. Total Synthesis of Monensin. 3. Stereocontrolled Total Synthesis of Monensin.
J. Am. Chem. Soc. 1979;
101: 262-263
DOI: 10.1021/ja00495a066.
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