Stereoselective Synthesis of Some Novel Heterocyclic Estrone Derivatives by Intramolecular 1,3-Dipolar Cycloaddition
Nitrones, Azomethine imines, 1, 3-dipolar cycloaddition, Lewis acid, Stereoselective synthesis
16,17-seco-3-Methoxyestra-1,3,5(10),16-tetraen-17-al undergoes intramolecular nitrone 1,3-dipolar cycloaddition with both hydroxylamine and N-methylhydroxylamine to produce a single isoxazolidine isomer in each case. The ring-closures of the hydrazones and the aldazine derived from the secoaldehyde lead to fused N-containing heterocycles via Lewis acid-induced cyclization of the intermediate azomethine imines.
Frank, E., Wolfling, J., Aukszi, B., Konig, V., Schneider, T. R., & Schneider, G. (2002). Stereoselective Synthesis of Some Novel Heterocyclic Estrone Derivatives by Intramolecular 1,3-Dipolar Cycloaddition. Tetrahedron, 58, (34), 6843 - 6849. https://doi.org/10.1016/S0040-4020(02)00741-X. Retrieved from https://nsuworks.nova.edu/cnso_chemphys_facarticles/4