oa South African Journal of Chemistry - The alkaloids of the Leguminosae : part II2. Hofmann degradative studies on calpurnine from Calpurnia subdecandra
|Article Title||The alkaloids of the Leguminosae : part II2. Hofmann degradative studies on calpurnine from Calpurnia subdecandra|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Author||M.A.*** Goosen, A.*, Kaplan, E.R.** & Osry|
|Publication Date||Oct 1966|
|Pages||57 - 61|
|Keyword(s)||13-hydroxyl group, 13-hydroxylupanine, 13-hydroxysparteine, Axial configuration, Comparative rate studies, Epimeric acetate, Hofmann degradation of 13-hydroxylupanine methiodide, Hofmann reaction and Hydrolysis of the acetate|
The axial configuration of the 13-hydroxyl group in 13-hydroxysparteine and hence 13-hydroxylupanine is confirmed by comparative rate studies on the hydrolysis of the acetate and of the epimeric acetate. Hofmann degradation of 13-hydroxylupanine methiodide gave a methine (II; R1 + R2=O, R3 = OH, R1 = H, R5 = CH3) and starting material. 13-Hydroxylupanine dihydromethine and 13-oxolupanine dihydromethine could not be degraded by the Hofmann reaction. The Hofmann degradation cannot therefore be used for the stepwise degradation of the D-ring in 13-hydroxylupanine.
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