Total Synthesis of (–)-Anaferine: a Further Ramification in a Diversity-Oriented Approach
| Autor: | Giada Tedesco, Elisa Bonandi, Dario Perdicchia, Daniele Passarella |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Pharmaceutical Science
bis-piperidine alkaloids 2-piperidine ethanol Withania somnifera Withania 010402 general chemistry 01 natural sciences Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Alkaloids lcsh:Organic chemistry Piperidines Drug Discovery Organic chemistry Physical and Theoretical Chemistry Natural product biology Ethanol 010405 organic chemistry Plant Extracts Organic Chemistry Total synthesis Stereoisomerism anaferine biology.organism_classification 0104 chemical sciences chemistry Chemistry (miscellaneous) Molecular Medicine Stereoselectivity Piperidine diversity-oriented synthesis |
| Zdroj: | Molecules Volume 25 Issue 5 Molecules, Vol 25, Iss 5, p 1057 (2020) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules25051057 |
| Popis: | 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 (&ndash )-anaferine, a bis-piperidine alkaloid present in Withania somnifera 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. |
| Databáze: | OpenAIRE |
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