Using Empirical Rules from 13C NMR Analysis to Determine the Stereochemistry of the Epoxide Located at the 5,6-position of Decalinic Systems 英文参考文献.docVIP

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Using Empirical Rules from 13C NMR Analysis to Determine the Stereochemistry of the Epoxide Located at the 5,6-position of Decalinic Systems 英文参考文献.doc

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Using Empirical Rules from 13C NMR Analysis to Determine the Stereochemistry of the Epoxide Located at the 5,6-position of Decalinic Systems 英文参考文献

323 Molecules 2000, 5 Using Empirical Rules from 13C NMR Analysis to Determine the Stereochemistry of the Epoxide Located at the 5,6-position of Decalinic Systems Raquel M. Cravero, Guillermo R. Labadie and Manuel Gonzalez Sierra IQUIOS (Instituto de Química Orgánica de Síntesis)-CONICET-Facultad de Cs. Bioquímicas y Far- macéuticas-Universidad Nacional de Rosario-Suipacha 531- 2000 Rosario-Santa Fe, Argentina E-mail: iquiosra@citynet.net.ar Abstract: An empiric rule derived from the analysis of the 13C NMR spectral data, allowed us to determine 5,6-epoxide stereochemistry on decalinic systems and a discussion of the scope and limitations of this rule and its extension to other carbon squeletons, is presented. Introduction 13C NMR and 1H NMR techniques are the most convenient methods for the elucidations of the oxirane ring stereochemistry in condensed policyclic systems, and have been widely used in the re- search of epoxides from natural sources [1-3]. Very often, however, the methods used consider mainly the effects of the oxirane ring on the γ car- bons [4-6]. Results and Discussion From the analysis of the 13C NMR data of a set of synthetic epoxides angularly substituted and placed on the C5-C6 position of decalin systems of known relative configurations; we could stablish an empirical correlation between the chemical shift difference of the oxirane carbons and the relative con- figuration of the epoxide. Therefore, using these chemical shift differences it is possible to predict the α or β orientation of the epoxide, that is, trans or cis stereochemistry of the epoxide relative to the C10 substituent (R3). R2 R2 R4 R1 R5 5 6 O 324 Molecules 2000, 5 Computing for each epoxide: ?δ (epoxide)= δ C-5 - δ C-6 , the subtraction between the 13C NMR chemi- cal shifts of both oxirane carbon signals, predicts: ?δ α-epoxide ?δ β-epoxide 5 ppm 3.8 ppm Besides, we will present a discussion of the scope and limi