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, Eva; Wolfling, Janos; Aukszi, Beatrix; Konig, Veronica; Schneider, Thomas R.; and Schneider, Gyula, "Stereoselective Synthesis of Some Novel Heterocyclic Estrone Derivatives by Intramolecular 1,3-Dipolar Cycloaddition" (2002). Chemistry and Physics Faculty Articles. 4.