Data di Pubblicazione:
2020
Citazione:
Total Synthesis of (–)-Anaferine: A Further Ramification in a Diversity-Oriented Approach / E. Bonandi, G. Tedesco, D. Perdicchia, D. Passarella. - In: MOLECULES. - ISSN 1420-3049. - 25:5(2020 Feb 27).
Abstract:
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 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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
bis-piperidine alkaloids; anaferine; diversity-oriented synthesis; 2-piperidine ethanol
Elenco autori:
E. Bonandi, G. Tedesco, D. Perdicchia, D. Passarella
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