17-HYDROXYLUPANINE AND 17-OXYLUPANINE

Silver oxide has been shown to oxidize lupanine to 17-hydroxylupanine. This base gives an anhydronium perchlorate identical with the "dehydrolupanine (NBS)" perchlorate of Marion and Leonard. 17-Oxylupanine is described, and, from the observation that it can be reduced catalytically to oxy...

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Bibliographic Details
Published in:Canadian journal of chemistry 1954-03, Vol.32 (3), p.235-241
Main Authors: Edwards, O. E, Clarke, F. H, Douglas, Bryce
Format: Article
Language:English
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Summary:Silver oxide has been shown to oxidize lupanine to 17-hydroxylupanine. This base gives an anhydronium perchlorate identical with the "dehydrolupanine (NBS)" perchlorate of Marion and Leonard. 17-Oxylupanine is described, and, from the observation that it can be reduced catalytically to oxysparteine, the stereochemistry of aphylline and oxysparteine is deduced. The basic strength of tertiary carbinolamines is discussed.
ISSN:0008-4042
1480-3291
DOI:10.1139/v54-031