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Synthesis and spectroscopic stereospecificity assay of the deuterated quinolizidine alkaloids (2S)-[2H]- and (2R)-[2H]-sparteine

✍ Scribed by Thomas Ebner; Jochen Rebell; Peter Fischer; Claus O. Meese

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
240 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

Borohydride reduction of the (+)-1,t-dehydrosparteiniuni salts 2a,b proceeds almost exclusively from the Si side, yielding, respectively, the stereoselectively (2S)(J)-deuterated (-)-sparteine l c from 2a and NaB2H,, and the (tR)(a)-deuterated (-)-sparteiite Id from 2b and NaBH,. Stereochemistry and isotopic purity of the deuterium label (298%) are established unequivocally by, iri con junction, 'H. ' H , and "C NMR spectroscopy.

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