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

Autor: Bonandi E; Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy., Tedesco G; Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy., Perdicchia D; Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy., Passarella D; Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2020 Feb 27; Vol. 25 (5). Date of Electronic Publication: 2020 Feb 27.
DOI: 10.3390/molecules25051057
Abstrakt: 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.
Databáze: MEDLINE
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