General methods of alkaloid synthesis. XI. Total synthesis of the sceletium alkaloid A-4 and an improved synthesis of (+/-)-mesembrine.
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16-Epi-Z-isositsirikine (1) has been isolated from the leaves of Catharanthus roseus and Rhazya stricta and identified through a combination of spectral interpretation and chemical correlation. The compound displayed antineoplastic activity in the KB test system in vitro and the P-388 test system in vivo.
[reaction: see text] (+)-Vellosimine has been synthesized enantiospecifically in 27% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled intramolecular palladium-coupling reaction as key steps.
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