Ancisheynine, the first n,c-coupled naphthylisoquinoline alkaloid: total synthesis and stereochemical analysis.
[reaction: see text] The first total synthesis of an N,C-coupled naphthylisoquinoline alkaloid-ancisheynine-was achieved by condensing a monocyclic diketone or the respective benzopyrylium salt with an aminonaphthalene. The presence of a rotationally hindered axis in ancisheynine was demonstrated by resolution of its two atropo-enantiomers by HPLC on a chiral phase with LC-CD coupling. The assignment of their axial configurations succeeded by quantum chemical CD calculations.
Bringmann
Gerhard
G
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzberg.de
Gulder
Tanja
T
Reichert
Matthias
M
Meyer
Frank
F
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry
D000470:Alkaloids; D007546:Isoquinolines; D009281:Naphthalenes; C514855:ancisheynine