Abstract
Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Acorus / chemistry*
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Catalysis
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Mercury / chemistry
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Molecular Structure
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Morpholines / chemical synthesis*
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Morpholines / chemistry
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Plant Roots / chemistry
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
Substances
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Alkaloids
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Morpholines
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Pyrroles
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Spiro Compounds
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acortatarin A
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acortatarin B
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Mercury