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Structure elucidation and carbon-13 NMR of the new aporphine alkaloid 3-hydroxyglaucine

✍ Scribed by Rönsch, Hasso ;Preiß, Alfred ;Schreiber, Klaus ;De Cördoba, Hilda Fernández

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
498 KB
Volume
1983
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

From the Lauraceae Ocotea bucherii has been isolated the 3‐hydroxy‐1,2,9,10‐tetramethoxy‐aporphine (1, 3‐hydroxyglaucine) whose structure was determined using spectroscopic methods. Application of various techniques in ^13^C NMR led to the spectral assignment of each skeletal carbon in [D~6~]DMSO as well as [D~6~]DMSO/NaOD. – The phenolate anion corresponding to 1 gave rise to pronounced, but opposite variations of the chemical shifts of the ipso and ortho carbons on the one hand or the para carbon on the other. This method proved to be decisive in confirming C‐3 as the carbon bearing the hydroxy group, whereas the alternative C‐2 was excluded.

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