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Synfacts 2021; 17(11): 1193
DOI: 10.1055/s-0040-1720724
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Lycopodine

Rezensent(en):
Erick M. Carreira
,
David M. Fischer
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
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Key words

(±)-lycopodine - Robinson annulation - Friedel–Crafts alkylation - Birch reduction

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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Publikationsverlauf

Artikel online veröffentlicht:
19. Oktober 2021

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