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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment.

Self-consistent reaction field solvation models derived from SCF-MO calculations are shown to be reliable in modeling the diastereoselectivity of the reactions of the anion and cation derived from (4S)-2,4-dimethyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione (1) at C(1) with electrophiles and nucleophiles, respectively. The found anti/syn ratio of compound 8, which is a seco-ent-ardeemin analogue obtained by alkylation of 1 with gramine methiodide, confirms this computational model. A close similarity between the calculated geometry of the piperazine ring in the anti isomers of 1,2,4-trialkyl derivatives and that deduced from their (1)H NMR (solution) and X-ray data has been also established.[1]


  1. Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment. Martín-Santamaría, S., Corzo-Suárez, R., Avendaño, C., Espada, M., Gago, F., García-Granda, S., Rzepa, H.S. J. Org. Chem. (2002) [Pubmed]
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