82884-90-0Relevant academic research and scientific papers
Heterocycles. XIII. Syntheses and Absolute Configurations of Chiral Benzophenanthridines
Harigaya, Yoshihiro,Takamatsu, Seiko,Yamaguchi, Hiroko,Onda, Masayuki
, p. 1244 - 1250 (2007/10/02)
Chiral benzophenanthridines have been synthesized.Aminolysis of the(-)-epoxyhydroxy lactone (3) with methylamine stereospecifically gives the (+)-trihydroxy lactam (5), from which the (+)-10b-hydroxychelidonine (7) and (+)-11-epichelidonine analogs (10) are derived.The absolute configurations of the compounds obtained are assigned on the basis of that of (-)-3 and the results obtained from the subsequent stereocontrolled reactions.The absolute configurations of (+)-7 and (+)-10 are confirmed by Horeau's method.Keywords- chiral benzophenanthridine; absolute configuration; circular dichroism; optical rotatory dispersion; proton magnetic resonance (contact shift)
