5a Crsoxystricrosidire: A Possible Intermediate in the Diogenes's of Insole Alkaloids
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The isolated and characterization of three amino acid glycosides from the roots of Rhazya orientalis are described. The relative stereochemistry of 5 a - carboxystrictosidine is determined by NMR and thermodynamic correlations with model compounds. The absolute stereochemistry of 5 a -carboxystrictosidine is established by molar rotation comparisons and biosynthesis and that of strictosamic acid by conversion into strictosidine. The macro-isolation of secologanin is described. Secologanin is used for the partial synthesis of the diastereoisomers of 5 a - carboxystrictosidine. Conformational analysis and the chemistry of these compounds leading to the assignments of their absolute configurations are presented. Final proof of the complete stereochemistry of 5 a – carboxystrictosidine and 5 a - carboxystrictosamic acid came from a direct comparison. The absence of vincoside and 5 – carboxyvincoside in Rhazya orientalis is demonstrated by radio – chemical dilution analysis. The biosynthesis of 5 a – carboxystrictosidine from loganin and L – tryptophan is established and it’s possible biogenetic significance is discussed.
The isolated and characterization of three amino acid glycosides from the roots of Rhazya orientalis are described. The relative stereochemistry of 5 a - carboxystrictosidine is determined by NMR and thermodynamic correlations with model compounds. The absolute stereochemistry of 5 a -carboxystrictosidine is established by molar rotation comparisons and biosynthesis and that of strictosamic acid by conversion into strictosidine. The macro-isolation of secologanin is described. Secologanin is used for the partial synthesis of the diastereoisomers of 5 a - carboxystrictosidine. Conformational analysis and the chemistry of these compounds leading to the assignments of their absolute configurations are presented. Final proof of the complete stereochemistry of 5 a – carboxystrictosidine and 5 a - carboxystrictosamic acid came from a direct comparison. The absence of vincoside and 5 – carboxyvincoside in Rhazya orientalis is demonstrated by radio – chemical dilution analysis. The biosynthesis of 5 a – carboxystrictosidine from loganin and L – tryptophan is established and it’s possible biogenetic significance is discussed.