The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

Title: The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

Volume: 9 Issue: 2

Author(s): Luciana Dalla-Vechia, Alexandra Dassonville-Klimpt, Philippe Grellier, Pascal Sonnet, Grace Gosmann and Simone C.B. Gnoatto

Affiliation:

Keywords: Antimalarial, Beckmann rearrangement, Beckmann fragmentation, triterpene, ursolic acid, thionyl chloride, aromatase, nitrogen, bioactive compounds, nitrile

Abstract: The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity.

Cite this article as:

Dalla-Vechia Luciana, Dassonville-Klimpt Alexandra, Grellier Philippe, Sonnet Pascal, Gosmann Grace and C.B. Gnoatto Simone, The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies, Letters in Organic Chemistry 2012; 9 (2) . https://dx.doi.org/10.2174/157017812800221708