Abstract
An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemistry*
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Amaryllidaceae Alkaloids / chemical synthesis*
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Amaryllidaceae Alkaloids / chemistry*
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Amaryllidaceae Alkaloids / pharmacology
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / chemistry*
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Antimalarials / pharmacology
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Circular Dichroism
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Isomerism
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Isoquinolines / chemistry*
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Models, Molecular
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Molecular Structure
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Phenanthridines / chemical synthesis*
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Phenanthridines / chemistry*
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Phenanthridines / pharmacology
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Plasmodium falciparum / drug effects
Substances
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Alkaloids
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Amaryllidaceae Alkaloids
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Antimalarials
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Heterocyclic Compounds, 4 or More Rings
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Isoquinolines
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Phenanthridines
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montanine
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pancracine
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hemanthamine