The Biogenetically Patterned Synthesis of Ajmaline |
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2N hydrochloric acid added Ajmalicine ajmaline alcohol XIX aldehyde aldehyde XVII alkaloid Alkylation amine amino acid amino acid XV Attempted Alkylation authentic benzene benzyl ether broad singlet butyraldehyde carbonate carbonyl catalyst chloroform CO₂H CO₂R compound condensation cyclization decomposition Deoxya Deoxyajmalal-B dicyclohexylcarbodiimide dilution diol dissolved distilled doublet Equilibration extraction Figure film cm-1 filtrate flask fragmentation reaction hydrochloric acid hydrogens aromatics iminium iminium salt indole infrared spectrum showed jmalal-B loganin material max The infrared melting point methanol methyl mixture was stirred ml of dry nitrogen atmosphere olefin organic layer osmium tetroxide oxidation pmr spectrum showed ppm in CDC13 racemic Rauwolfia Serpentina reaction mixture recrystallized resulting RO₂C room temperature rotary evaporator rotary evaporator gave saturated aqueous sodium singlet sodium borohydride solution was stirred solvent spectrum showed absorptions suspension synthesis of ajmaline Tamelen tetrahydrofuran three hydrogens toluenesulfonic acid tosylate tryptophan ultraviolet white solid yield он