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- W2950583469 abstract "L-Tryptophan methyl ester reacts with acetaldehyde in a Pictet-Spengler condensation to give a 2.5:1 mixture of the stereoisomers (1S,3S)-2 and (1R,3S)-2. These were converted by ammonolysis into the corresponding amides (1S,3S)-3 or (1R,3S)-3. On methylation of (1S,3S)-3 or (1R,3S)-3 the corresponding 2-methylcarbolineamide (1S,3S)-4 or (1R,3S)-4 were obtained. Dehydration of (1S,3S)-4 or (1R,3S)-4 affords 2-methylcarbolinenitrile (1S,3S)-5 or (1R,3S)-5. After reduction with NaBH4 (1S,3S)-5 or (1R,3S)-5 was decyanated and the title compound (1S)-6 or (1R)-6 was obtained. With NOE experiments their stereochemistry were determined and their optical purities were confirmed by measurements using a chiral shift reagent." @default.
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- W2950583469 date "1993-02-12" @default.
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- W2950583469 title "Synthesis of Enantiomerically Pure Tetrahydro-2-methylharman" @default.
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- W2950583469 doi "https://doi.org/10.1002/jlac.199319930125" @default.
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