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Structure elucidation and carbon‐13 NMR of the new aporphine alkaloid 3‐hydroxyglaucine
Author(s) -
Rönsch Hasso,
Preiß Alfred,
Schreiber Klaus,
De Cördoba Hilda Fernández
Publication year - 1983
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198319830503
Subject(s) - chemistry , lauraceae , aporphine , chemical shift , carbon 13 nmr , alkaloid , carbon fibers , stereochemistry , botany , materials science , composite number , composite material , biology
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.