Collect. Czech. Chem. Commun. 2000, 65, 789-796

On the Reaction of Deacetylvindoline with Thionyl Chloride

Josef Hájíčeka,* and Vladimír Hanušb

a Research Institute of Pharmacy and Biochemistry, Kouřimská 17, 130 60 Prague 3, Czech Republic
b J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 182 23 Prague 8, Czech Republic


Reaction of deacetylvindoline (2) with excess thionyl chloride gave rise to hexacyclic 6,10-dichloro-6,17-epithio-11-methoxy-1-methyltabersonine (4) as a single product in 43.5% yield. The structure was deduced from 1H and 13C 1D and 2D NMR experiments as well as from mass spectra. A tentative mechanism of this complex transformation was also proposed.

Keywords: Indole alkaloids; Deacetylvindoline; Chlorination; Cyclizations; Sulfur; NMR spectroscopy; Mass spectrometry; Reaction mechanism.

References: 8 live references.