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

Bonandi, Elisa; Tedesco, Giada; Perdicchia, Dario; Passarella, Daniele; Costantino, Valeria

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.

NATURAL products; WITHANIA somnifera; ALKALOIDS; RESEARCH teams; ETHANOL; ISOQUINOLINE alkaloids

Molecules, 2020, Vol 25, Issue 5, p1057

1420-3049

Academic Journal

10.3390/molecules25051057