Synthetic studies towards dendridine A: synthesis of hemi-dendridine A acetate by Fischer indolization |
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Authors: | Emily M BoydJonathan Sperry |
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Institution: | School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand |
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Abstract: | A short synthesis of hemi-dendridine A acetate has been accomplished. The synthesis is based on a modified Fischer indolization that represents a rare example of the single-step synthesis of a 7-oxytryptamine from an ortho-oxygenated phenylhydrazine. The synthetic route required developing an efficient synthesis of N-acetyl-2-pyrroline, the key coupling partner for the modified Fischer indolization. Some interesting chemistry associated with the abnormal Fischer indolization has been uncovered, whereby two molecules of the phenylhydrazine substrate combined along the abnormal reaction pathway, affording an unusual N-phenylindoleamine product. |
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Keywords: | Dendridine A Bisindole Abnormal Fischer indolization Alkaloid Tryptamine |
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