157183-10-3Relevant academic research and scientific papers
Concise Asymmetric Syntheses of (+)- and (-)-Tetraponerine-8, (+)- and (-)-Tetraponerine-7, and their Ethyl Homologues. A Correction of the Structures of Tetraponerine-3, and -7.
Macours, P.,Braekman, J. C.,Daloze, D.
, p. 1415 - 1428 (2007/10/02)
(+)- and (-)-T-8, (+)- and (-)-9-epi-T8, and their ethyl homologues were synthesized in six steps and 27percent overall yield from chiral acetylenic sulfoxide (+)-7a or (+)-7b, via a cycloaddition reaction with 3,4,5,6-tetrahydropyridine-1-oxide, and chromatographic separation of the resulting diastereoisomeric Δ4-isoxazolines.Comparison of the spectral properties of the synthetic (+)-9-epi-T-8 with those of natural (+)-T-7 and (+)-T-3 led us to correct the structures of the latter two compounds.The absolute configuration of (+)-T-4 was determined to be 5R,9S,11R, and those of (+)-T-7 and (+)-T-3 to be 5R,9R,11R by comparison of their CD curves with those of the synthetic compounds.
Synthesis of enantiomeric β-amino ketones via 1,3-dipolar cycloaddition and chromatographic resolution
Louis, Chantal,Mill, Sibel,Mancuso, Vincent,Hootele, Claude
, p. 1347 - 1350 (2007/10/02)
The cycloaddition reactions of 3,4,5,6-tetrahydropyridine 1-oxide 1 with the homochiral alkynyl sulfoxides 6a-e proceed in high yield to afford, with low asymmetric induction, mixtures of diastereomeric isoxazolines that are readily separated by column chromatography.The resolved isoxazolines can be subsequently converted, by hydrogenolysis, to enantiomeric β-amino ketones.
