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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.
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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.
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Publication History
Article published online:
17 January 2023
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