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

Molecules

Elisa Bonandi¹  Dario Perdicchia¹  Daniele Passarella¹  Giada Tedesco¹ 

[1] Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy;

关键词: bis-piperidine alkaloids;    anaferine;    diversity-oriented synthesis;    2-piperidine ethanol;   

DOI  :  10.3390/molecules25051057

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown