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SYNTHESES AND ABSOLUTE CONFIGURATION ASSIGNMENTS OF MONO- AND DI-SUBSTITUTED CHIRAL QUINOLINE ALKALOIDS OBTAINED BY ASYMMETRIC OXIDATION

  作者 BARR STEPHEN A; BOYD DEREK R; SHARMA NARAIN D; LOKE PUI L  
  选自 期刊  Heterocycles;  卷期  2009年79-1;  页码  831-850  
  关联知识点  
 

[摘要]Mono- and di-substituted quinoline, 2-quinolone, dihydrofuroquinoline and dihydropyranoquinoline alkaloids have been synthesised with enantiomeric excess values of > 90%, via asymmetric epoxidation, or asymmetric dihydroxylation of the corresponding alkene precursors. The absolute configurations of isobalfourodine, psi-balfourodine, psi-isobalfourodine, isobalfourodinium methiodide, balfourolone, hydroxylunidine, orixine, nororixine, isopteleflorine, O-acetylisopteleflorine, O-methylhydroxylunium methiodide and hydroxylunine have been rigorously determined by a combination of circular dichroism spectroscopy, ozonolysis, and stereochemical correlation. Of these, the absolute configurations of six alkaloids were previously unknown and six were assigned incorrect configurations in the literature.

 
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