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Synfacts 2021; 17(11): 1193
DOI: 10.1055/s-0040-1720724
DOI: 10.1055/s-0040-1720724
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Lycopodine
Stork G,
Kretchmer RA,
Schlessinger RH.
Columbia University, New York, USA
The Stereospecific Total Synthesis of dl-Lycopodine.
J. Am. Chem. Soc. 1968;
90: 1647-1648
DOI: 10.1021/ja01008a042
The Stereospecific Total Synthesis of dl-Lycopodine.
J. Am. Chem. Soc. 1968;
90: 1647-1648
DOI: 10.1021/ja01008a042
Significance
In 1968, Stork and co-workers reported the total synthesis of the alkaloid natural product (±)-lycopodine. This natural product, isolated over 130 years ago, is part of a family of compounds that have long attracted attention for the bioactivity and structural complexity.
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Comment
Cyclization followed by conjugate addition furnishes ketone C, which is then elaborated to amide E. After Friedel–Crafts alkylation and functional group modulation, enol ether H is subjected to ozonolysis and selenium dioxide-mediated oxidation. Keto ester I then rapidly gave access to the natural product.
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Publication History
Article published online:
19 October 2021
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