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Synthesis and spectroscopic stereospecificity assay of the deuterated quinolizidine alkaloids (2S)‐[ 2 H]‐ and (2R)‐[ 2 H]‐sparteine
Author(s) -
Ebner Thomas,
Rebell Jochen,
Fischer Peter,
Meese Claus O.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270417
Subject(s) - sparteine , chemistry , deuterium , stereospecificity , borohydride , deuterium nmr , quinolizidine , nuclear magnetic resonance spectroscopy , stereochemistry , kinetic isotope effect , medicinal chemistry , alkaloid , organic chemistry , catalysis , physics , quantum mechanics
Abstract Borohydride reduction of the (+)−1,2‐dehydrosparteinium salts 2a,b proceeds almost exclusively from the Si side, yielding, respectively, the stereoselectively (2S)(β)‐deuterated (−)‐sparteine 1c from 2a and NaB 2 H 4 , and the (2R)(α)‐deuterated (−)‐sparteine 1d from 2b and NaBH 4 . Stereochemistry and isotopic purity of the deuterium label (≧98%) are established unequivocally by, in conjunction. 1 H, 2 H, and 13 C NMR spectroscopy.