38681-18-4

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Nupharolutine is used as a pharmaceutical compound for its potential therapeutic applications. Its alkaloid nature and specific properties make it a candidate for further research and development in the field of medicine.
Used in Chemical Research:
(-)-Nupharolutine is used as a research compound for studying its chemical properties, structure, and potential interactions with other molecules. This can contribute to the understanding of its pharmacological effects and possible applications in various fields.
Used in Natural Product Chemistry:
(-)-Nupharolutine is used as a representative example of a natural product derived from plants, specifically the rhizomes of Nuphar luteum. Its study can provide insights into the chemical diversity and potential bioactive properties of natural products.

References

Wrobel et al., Can. J. Chern., 50, 1831 (1972)

Upstream product

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Relevant academic research and scientific papers

Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions

(Chemical Equation Presented). In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.

A FACILE SYNTHESIS OF A NUPHAR ALKALOID, NUPHAROLUTINE

A regio- and stereoselective synthesis of (+/-)-nupharolutine (2) was achieved starting from 3-methylpyridine by utilizing the SnCl2-effected reaction of endoperoxide of a 1,2-dihydropyridine derivative (5).