Producción Científica Profesorado

The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides

Torres Valencia, J. Jesús Martín


Adriana Ortiz-León, J. Martín Torres-Valencia, J. Jesús Manríquez-Torres, José G. Alvarado-Rodríguez, Carlos M. Cerda-García-Rojas, Pedro Joseph-Nathan, Tetrahedron: Asymmetry, 2017, 28 (2), 367?373


The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastereoselectivity in favour of the (11S)-stereoisomer was 86?98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastereoselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters.

Producto de Investigación

Artículos relacionados

Purification, Biochemical Characterization, and Bioactive Properties of a Lectin Purified from the S...

Detection of Cytotoxic Activity of Lectin on Human Colon Adenocarcinoma (Sw480) and Epithelial Cervi...

Effect of the particle size on the activity of MoOxCy catalysts for the isomerization of heptane

Antioxidant constituents from Geranium bellum Rose

Estudio químico de cinco plantas mexicanas de uso común en la medicina tradicional

Lead, Cadmium and Cobalt (Pb, Cd, and Co) Leaching of Glass-Clay Containers by pH Effect of Food