On the reaction of deacetylvindoline with thionyl chloride

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 H-1 and C-13 1D and 2D NMR experiments as well as from mass spectra. A tentative mec...

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Bibliographic Details
Published inCollection of Czechoslovak chemical communications Vol. 65; no. 5; pp. 789 - 796
Main Authors Hajicek, J, Hanus
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
cyclizations
indole alkaloids
reaction mechanism
sulfur
mass spectrometry
chlorination
NMR spectroscopy
deacetylvindoline
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Summary: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 H-1 and C-13 1D and 2D NMR experiments as well as from mass spectra. A tentative mechanism of this complex transformation was also proposed.
ISSN:0010-0765
DOI:10.1135/cccc20000789