Geneserine and geneseroline revisited: acid-base catalyzed equilibria of hexahydropyrrolo-[2,3-b]-indole N-oxides with hexahydro-1,2-oxazino-[5,6-b]-indoles.
It is shown that geneserine [2] and geneseroline [4] convert with acid into salts of physostigmine N-oxide [3] and geneseroline N-oxide [5], respectively. Structure assignments were made on the basis of chemical conversions, 1H-nmr analysis of 2-5, and an X-ray analysis of 5 as its hydrochloride.
Yu
Q S
QS
Laboratory of Analytical Chemistry, NIDDK, Bethesda, Maryland 20892.
Yeh
H J
HJ
Brossi
A
A
Flippen-Anderson
J L
JL
D000470:Alkaloids / Q000032:analysis*; D002384:Catalysis; D055598:Chemical Phenomena; D002621:Chemistry; D003461:Crystallography; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
D000470:Alkaloids; C060404:geneseroline; C060406:geneserine