The oxidation of diterpenoid alkaloids

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DOIResolve DOI: http://doi.org/10.1139/v65-315
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume43
Issue8
Pages23362344; # of pages: 9
AbstractThe highly oxygenated diterpenoid alkaloids possessing the same C—N ring structure fall into two groups: group A containing the aconitine-like bases in which the C-6 methoxyl is α-oriented, and group B containing the lycoctonine-like bases in which the C-6 methoxyl is β-oriented. The alkaloids of both groups are oxidized rapidly at room temperature by neutral potassium permanganate. The oxidation dealkylates the amino group in the bases of group A giving rise to secondary bases while it converts the bases of group B to the corresponding lactams. The different course of the oxidation from one group to the other is due to the different orientation of the C-6 methoxyl, and can be used to determine the stereochemistry at C-6.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada
Peer reviewedYes
NPARC number21274428
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Record identifier35ad95c9-d2fa-4f9f-8fff-f28bec99c156
Record created2015-03-12
Record modified2016-05-09
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