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Access to the (+)- or (-)-Enantiomers of the Bioactive C-19 Methyl-Substituted Sarpagine/Macroline/Ajmaline Alkaloids from either d - or L-Tryptophan
Rahman, M. T., & Cook, J. M. (2019). The ambidextrous Pictet-Spengler reaction: Access to the (+)- or (-)-Enantiomers of the Bioactive C-19 Methyl-Substituted Sarpagine/Macroline/Ajmaline Alkaloids from either d - or L-Tryptophan. Synthesis, 51(9), 1980-1988. https://doi.org/10.1055/s-0037-1610687
Depicted in the following is the proof of concept, which is important to illustrate the full potential of the ambidextrous Pictet-Spengler (P-S) reaction. Previously, both d -tryptophan and l -tryptophan were employed to synthesize the key intermediates toward the natural enantiomers of C-19 methyl-substituted alkaloids. Now the enantiomeric series of the same key intermediates could also be synthesized from both d - or l -tryptophan in high yield and optical purity via this P-S/Dieckmann protocol. One can make either the natural or the unnatural alkaloids from either of the chiral starting amino acid esters, stereo- and enantiospecifically for biological screening.