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
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.
