Solution and crystal conformations of myrionine, a new 8beta-alkyl-cis-decahydroquinoline of Myrioneuron nutans.
Myrionine (1), a new 8beta-alkyl-cis-decahydroquinoline, was isolated from Myrioneuron nutans. Its structure was determined by spectral methods and then confirmed by X-ray analysis and total synthesis. In solution, 1 gives rise to an N-in/N-out equilibrium. The solvent has weak influence on the N-in/N-out ratio for myrionine (1), whereas together with the anions, it plays an important role for myrionine hydrochloride (9) and hydroiodide (10). The two N-in and N-out conformations obtained separately by crystallization of 9 and 10, respectively, were analyzed by X-ray diffraction.
Pham
Van Cuong
VC
Laboratoire de Chimie des Substances Naturelles - UMR 5154 CNRS, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75005 Paris, France.
Jossang
Akino
A
Chiaroni
Angèle
A
Sévenet
Thierry
T
Nguyen
Van Hung
VH
Bodo
Bernard
B
D003460:Crystallization; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D019666:Rubiaceae / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry
D011804:Quinolines; D012996:Solutions; C524012:myrionine