Abstract
Palladium catalyzed asymmetric allylic alkylation reaction of an amine with two equivalents of butadiene monoxide allows for the expedient synthesis of trans- and cis-2,5-dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of iminosugar natural products was demonstrated with the short and high yielding asymmetric syntheses of (+)-DMDP, and (-)-bulgecinine. In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkylation
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Catalysis
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Epoxy Compounds / chemistry*
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Glycopeptides / chemical synthesis*
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Glycopeptides / chemistry
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Imino Pyranoses / chemical synthesis
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Imino Pyranoses / chemistry
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Mannitol / analogs & derivatives*
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Mannitol / chemical synthesis
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Mannitol / chemistry
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Nuclear Magnetic Resonance, Biomolecular
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Palladium / chemistry
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Pyrrolidines / chemical synthesis*
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Pyrrolidines / chemistry
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Stereoisomerism
Substances
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2,5-dideoxy-2,5-imino-D-mannitol
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Alkaloids
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Epoxy Compounds
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Glycopeptides
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Imino Pyranoses
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Pyrrolidines
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broussonetine G
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Mannitol
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3,4-epoxy-1-butene
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Palladium
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bulgecin