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DOI: 10.1055/s-0040-1720724
Total Synthesis of (±)-Lycopodine
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.
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.
Publikationsverlauf
Artikel online veröffentlicht:
19. Oktober 2021
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