Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach

The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing c...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-02, Vol.25 (5), p.1057
Main Authors: Bonandi, Elisa, Tedesco, Giada, Perdicchia, Dario, Passarella, Daniele
Format: Article
Language:English
Subjects:
2-piperidine ethanol
Alcohol
Alkaloids
Alkaloids - chemical synthesis
Alkaloids - chemistry
anaferine
bis-piperidine alkaloids
Cytotoxicity
diversity-oriented synthesis
Ethanol
Ethanol - chemistry
Laboratories
Libraries
Microorganisms
Natural products
Nitrogen
Piperidine
Piperidines - chemistry
Plant Extracts - chemistry
Stereoisomerism
Stereoselectivity
Withania - chemistry
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Summary:The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing commercially available 2-piperidine ethanol as a versatile precursor. Here, we report the exploration of another ramification of our DOS approach, that led us to the stereoselective total synthesis of (-)-anaferine, a bis-piperidine alkaloid present in extract. This natural product was obtained in 9% overall yield over 13 steps, starting from a key homoallylic alcohol previously synthesised in our laboratory. Therefore, the collection of piperidine-derivatives accessible from 2-piperidine ethanol was enriched with a new, diverse scaffold.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25051057