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The total syntheses of vallesiachotamine 1 and isovallesiachotamine 2, indole alkaloids from dogbane plants, which are formed in vitro and in vivo from tryptamine and secologanin, were achieved by addition of silicon-stabilized anions to pyridinium salts and subsequent Pictet-Spengler reaction as the key reaction steps. Synthetic 1 and 2 were identical (except in their chiroptic properties) with authentic samples from plant cultures.
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Spitzner et al. (1984) studied this question.
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