The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)- piperidine-1-carboxylic acid tert-butyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks.
Short Enantioselective Synthesis of Sedridines, Ethylnorlobelols and Coniine via Reagent-Based Differentiation / D. Passarella, A. Barilli, F. Belinghieri, S. Fassi, S. Riva, A. Sacchetti, A. Silvani, B. Danieli. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 16:13(2005), pp. 2225-2229. [10.1016/j.tetasy.2005.05.032]
Short Enantioselective Synthesis of Sedridines, Ethylnorlobelols and Coniine via Reagent-Based Differentiation
D. Passarella;A. Barilli;F. Belinghieri;A. Sacchetti;A. Silvani;B. Danieli
2005
Abstract
The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)- piperidine-1-carboxylic acid tert-butyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks.Pubblicazioni consigliate
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