Synthesis of thalprzewalskiinone, a revision of structure.
A direct comparison of the spectral data for synthetic 2-methyl-6,7-dimethoxy-3'-methoxy-4'-hydroxyoxobenzylisoquinoline iodide (1) and its positional isomer 2-methyl-6,7-dimethoxy-3'-hydroxy-4'-methoxyoxobenzylisoquinoline iodide (2) with the data obtained for the oxobenzylisoquinoline alkaloid thalprzewalskiinone revealed that the original structural assignment of the alkaloid as 1 was in error. These results mandate the revision of structure of thalprzewalskiinone to 2-methyl-6,7-dimethoxy-3'-hydroxy-4'-methoxyoxobenzylisoquinoline iodide (2).
Al-Howiriny
T A
TA
Department of Pharmaceutical Sciences, School of Pharmacy, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, USA.
Zemaitis
M A
MA
Gao
C Y
CY
Hadden
C E
CE
Martin
G E
GE
Lin
F T
FT
Schiff
P L
PL
D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet
D004365:Drugs, Chinese Herbal; D007202:Indicators and Reagents; D007546:Isoquinolines; C433624:thalprzewalskiinone