Syntheses and absolute configuration assignments of mono- and di-substituted chiral quinoline alkaloids obtained by asymmetric oxidation
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 alken
Barr, Stephen A.,Boyd, Derek R.,Sharma, Narain D.,Loke, Pui L.
experimental part
p. 831 - 850
(2009/12/01)
Absolute stereochemistry of (-)-preorixine and related compounds
The absolute stereochemistry of the C-2' position of (-)-preorixine, postulated to be an important biosynthetic precursor of various quinoline alkaloids, was assigned as R by the combination of its chemical transformation and the extended Mosher method. The stereochemistry of the C- 2' position of (+)-orixine was also concluded to be R, establishing that no inversion occurred when (-)-preorixine was transformed into (+)-orixine.
Funayama, Shinji,Murata, Kiyoshi,Nozoe, Shigeo
p. 1885 - 1889
(2007/10/03)
ISOLATION OF (-)-PREORIXINE, A POSTULATED BIOSYNTHETIC KEY INTERMEDIATE OF (+)-ORIXINE AND RELATED QUINOLINE ALKALOIDS, FROM THE STEMS OF ORIXA JAPONICA
A prenyl quinoline alkaloid (-)-preorixine was isolated from the stems of Orixa japonica (Rutaceae) and its structure was elucidated to be (-)-3-(2S,3-epoxy-3-methylbutyl)-2,4-dimethoxy-7,8-methylenedioxyquinoline. (-)-Preorixine is postulated as a biosynthetic key intermediate of (+)-orixine and related compounds.