Conformationally Restricted Amino Cyclopropane-Fused Lactones from Mannich Bases
Mauricio Bahena Garcia1, Victor Fadare1, Zarko Boskovic1
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.
Abstract:
We converted easily accessible Mannich bases into cyclopropane-fused lactones by combining a photochemical reaction using simple 370 nm LED source with acid-catalyzed hydrolysis and lactonization. The alcohol functional group generated in the photochemical reaction was used in the subsequent step. This three-step sequence rapidly generates conformationally restricted amino cyclopropane-fused γ-, δ-, and ε-lactones. We also devised a method to kinetically monitor the cyclopropanation reaction and to analyze the data through a full-spectrum quantitation approach.
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